Progress in the chemical synthesis of brassinosteroids

Brassinosteroids

Fujioka, S., & Sakurai, A. (1997) · Natural Product Reports · doi:10.1039/np9971400001 · Cited by 124 · see citing works

Identification of a New Brassinosteroid, Cathasterone, in Cultured Cells ofCatharanthus roseusas a Biosynthetic Precursor of Teasterone

Fujioka, S., Inoue, T., Takatsuto, S., Yanagisawa, T., Yokota, T., & Sakurai, A. (1995) · Bioscience Biotechnology and Biochemistry · doi:10.1271/bbb.59.1543 · Cited by 81 · see citing works

Brassinosteroids: A new way to define the structural requirements

Brosa, C., Capdevila, J. M., & Zamora, I. (1996) · Tetrahedron · doi:10.1016/0040-4020(95)01065-3 · Cited by 76 · see citing works

Purification and Identification of New Acyl-conjugated Teasterones in Lily Pollen

Asakawa, S., Abe, H., Nishikawa, N. S., Natsume, M., & Koshioka, M. (1996) · Bioscience Biotechnology and Biochemistry · doi:10.1271/bbb.60.1416 · Cited by 51 · see citing works

New synthetic brassinosteroids: a 5α-hydroxy-6-ketone analog with strong plant growth promoting activity

Brosa, C., Soca, L., Terricabras, E., Ferrer, J. C., & Alsina, A. (1998) · Tetrahedron · doi:10.1016/s0040-4020(98)00743-1 · Cited by 43 · see citing works

Synthesis and bioactivity evaluation of brassinosteroid analogs

Ramirez, J. A., Centurión, O. T., Gros, E. G., & Galagovsky, L. R. (2000) · Steroids · doi:10.1016/s0039-128x(00)00093-3 · Cited by 43 · see citing works

New Developments in Brassinosteroid Research

Adam, G. V., Porzel, A., Schmidt, J. O., Schneider, B., & Voigt, B. (1995) · Studies in natural products chemistry · doi:10.1016/s1572-5995(96)80033-0 · Cited by 41 · see citing works

Teasterone 3-Myristate: A New Type of Brassinosteroid Derivative inLilium longiflorumAnthers

Asakawa, S., Abe, H., Kyokawa, Y., Nakamura, S., & Natsume, M. (1994) · Bioscience Biotechnology and Biochemistry · doi:10.1271/bbb.58.219 · Cited by 39 · see citing works

Flavonoids and bioactive coumarins of Tordylium apulum

Kofinas, C., Chinou, İ., Loukis, A. E., Harvala, C., Maillard, M. P., & Hostettmann, K. (1998) · Phytochemistry · doi:10.1016/s0031-9422(98)00018-1 · Cited by 38 · see citing works

Synthesis and biological evaluation of extra-hydroxylated brassinolide analogs

Seto, H., Fujioka, S., Koshino, H., Yoshida, S., Tsubuki, M., & Honda, T. (1999) · Tetrahedron · doi:10.1016/s0040-4020(99)00427-5 · Cited by 36 · see citing works

Improved synthesis of brassinolide

McMorris, T. C., Chavez, R. G., & Patil, P. A. (1996) · Journal of the Chemical Society Perkin Transactions 1 · doi:10.1039/p19960000295 · Cited by 32 · see citing works

Concise, Improved Procedure for the Synthesis of Brassinolide and Some Novel Side-Chain Analogues

Back, T. G., Baron, D. L., Luo, W., & Nakajima, S. K. (1997) · The Journal of Organic Chemistry · doi:10.1021/jo961854y · Cited by 32 · see citing works

Stereocontrolled Synthesis of the 22E,24β(S)-Trifluoromethyl Steroidal Side Chain and Its Application to the Synthesis of Fluorinated Analogues of Naturally Occurring Sterols

Jiang, B., Liu, Y., & Zhou, W. (2000) · The Journal of Organic Chemistry · doi:10.1021/jo000059o · Cited by 30 · see citing works

Regioselective oxyfunctionalization of brassinosteroids by methyl(trifluoromethyl)dioxirane: Synthesis of 25-hydroxy-brassinolide and 25-hydroxy-24-epibrassinolide by direct C-H insertion

Voigt, B., Porzel, A., Golsch, D., Adam, W., & Adam, G. (1996) · Tetrahedron · doi:10.1016/0040-4020(96)00587-x · Cited by 30 · see citing works

Plant Chromosomes: Brassinosteroids in the spotlight

Clouse, S. D. (1996) · Current Biology · doi:10.1016/s0960-9822(09)00442-4 · Cited by 28 · see citing works

Highly Stereocontrolled Formal Synthesis of Brassinolide via Chiral Sulfoxide-Directed SN2‘ Reactions

Marino, J. P., de Dios, A., Anna, L. J., & de la Pradilla, R. F. (1996) · The Journal of Organic Chemistry · doi:10.1021/jo951264k · Cited by 28 · see citing works

Structure–activity studies of brassinolide B-ring analogues

Baron, D. L., Luo, W., Janzen, L., Pharis, R. P., & Back, T. G. (1998) · Phytochemistry · doi:10.1016/s0031-9422(98)00367-7 · Cited by 26 · see citing works

Synthesis of 24-epiteasterone, 24-epityphasterol and their B-homo-6a-oxalactones from ergosterol

Voigt, B., Schmidt, J., & Adam, G. (1996) · Tetrahedron · doi:10.1016/0040-4020(95)01042-4 · Cited by 25 · see citing works

Synthesis of (22R, 25R)-2α,3α,26-Trihydroxy-5α-furostan-6-one

Iglesias‐Arteaga, M. A., Gil, R. P., Lara, V. L., Martínez, C. S. P., & Manchado, F. C. (1998) · Synthetic Communications · doi:10.1080/00397919808007008 · Cited by 25 · see citing works

Cryptolide, a New Brassinolide Catabolite with a 23-oxo group from Japanese cedar pollen/anther and its synthesis

Watanabe, T., Yokota, T., Shibata, K., Nomura, T., Seto, H., & Takatsuto, S. (2000) · Journal of Chemical Research · doi:10.3184/030823400103165734 · Cited by 25 · see citing works

Monitoring brassinosteroid biosynthetic enzymes by fluorescent tagging and HPLC analysis of their substrates and products

Winter, J. (1999) · Phytochemistry · doi:10.1016/s0031-9422(98)00760-2 · Cited by 22 · see citing works

Síntesis de espirobrasinoesteroides análogos de la 6-desoxocastasterona

Iglesias‐Arteaga, M. A., Lara, V. L., Martı́nez, C. P., & Manchado, F. C. (1997) · Química Nova · doi:10.1590/s0100-40421997000400004 · Cited by 22 · see citing works

Synthesis of secasterone and further epimeric 2,3- epoxybrassinosteroids

Voigt, B., Takatsuto, S., Yokota, T., & Adam, G. (1995) · Journal of the Chemical Society Perkin Transactions 1 · doi:10.1039/p19950001495 · Cited by 22 · see citing works

Effect of Chain Length and Ring Size of Alkyl and Cycloalkyl Side-Chain Substituents upon the Biological Activity of Brassinosteroids. Preparation of Novel Analogues with Activity Exceeding that of Brassinolide

Back, T. G., Janzen, L. M., Nakajima, S. K., & Pharis, R. P. (2000) · The Journal of Organic Chemistry · doi:10.1021/jo9917947 · Cited by 22 · see citing works

Synthesis and Biological Activity of 25-Methoxy-, 25-Fluoro-, and 25-Azabrassinolide and 25-Fluorocastasterone: Surprising Effects of Heteroatom Substituents at C-25

Back, T. G., Janzen, L. M., Nakajima, S. K., & Pharis, R. P. (1999) · The Journal of Organic Chemistry · doi:10.1021/jo990312o · Cited by 21 · see citing works

Bioactivity of brassinolide methyl ethers

Luo, W., Janzen, L. M., Pharis, R. P., & Back, T. G. (1998) · Phytochemistry · doi:10.1016/s0031-9422(97)00881-9 · Cited by 19 · see citing works

A general approach to synthesis of labeled brassinosteroids: Preparation of [25,26,27-2H7]brassinolide with 60% isotopic purity from the parent brassinolide

Seto, H., Fujioka, S., Koshino, H., Yoshida, S., Watanabe, T., & Takatsuto, S. (1998) · Tetrahedron Letters · doi:10.1016/s0040-4039(98)01636-0 · Cited by 19 · see citing works

A formal synthesis of brassinolide

Schmittberger, T., & Uguen, D. (1997) · Tetrahedron Letters · doi:10.1016/s0040-4039(97)00474-7 · Cited by 19 · see citing works

Synthesis and biological activity of 6a-carbabrassinolide: B-ring homologation of 6-oxo-steroid to 6-oxo-7a-homosteroid with trimethylsilyldiazomethane-boron trifluoride etherate

Seto, H., Fujioka, S., Koshino, H., Hayasaka, H., Shimizu, T., Yoshida, S., & Watanabe, T. (1999) · Tetrahedron Letters · doi:10.1016/s0040-4039(99)00186-0 · Cited by 17 · see citing works

Labelling of biogenetic brassinosteroid precursors

Kolbe, A., Schneider, B., Voigt, B., & Adam, G. (1998) · Journal of Labelled Compounds and Radiopharmaceuticals · doi:10.1002/(sici)1099-1344(199802)41:2 · Cited by 17 · see citing works

Stereoselective synthesis of a new hexanor(C23–C28)castasterone-20,22-ethyl diether from 16-dehydropregnenolone acetate and its plant growth promoting activity

Hazra, B. G., Basu, S., Bahule, B. B., Pore, V. S., Vyas, B. N., & Ramraj, V. M. (1997) · Tetrahedron · doi:10.1016/s0040-4020(97)00186-5 · Cited by 16 · see citing works

Synthesis of New Naturally Occurring 6-Deoxo Brassinosteroids

Takatsuto, S., Watanabe, T., Fujioka, S., & Sakurai, A. (1997) · Journal of Chemical Research Synopses · doi:10.1039/a608323d · Cited by 15 · see citing works

Synthesis of 24-epicathasterone and related brassinosteroids with modified side chain

Voigt, B., Porzel, A., Bruhn, C., Wagner, C., Merzweiler, K., & Adam, G. (1997) · Tetrahedron · doi:10.1016/s0040-4020(97)10146-6 · Cited by 15 · see citing works

Synthesis of Cathasterone and its Related Putative Intermediates in Brassinolide Biosynthesis†

Takatsuto, S., Kuriyama, H., Noguchi, T., Suganuma, H., Fujioka, S., & Sakurai, A. (1997) · Journal of Chemical Research Synopses · doi:10.1039/a704788f · Cited by 14 · see citing works

New Method of Preparation of Brassinosteroids

Kohout, L. (1994) · Collection of Czechoslovak Chemical Communications · doi:10.1135/cccc19940457 · Cited by 14 · see citing works

A convenient stereoselective synthesis of castasterone and its analogues using arsenic ylides

Werner, F., Parmentier, G., Luu, B., & Dinan, L. N. (1996) · Tetrahedron · doi:10.1016/0040-4020(96)00186-x · Cited by 13 · see citing works

Pregnane-Type Brassinosteroids with a Four-Carbon Ester Functionality in Position 20

Kohout, L., Kasal, A., & Strnad, M. (1996) · Collection of Czechoslovak Chemical Communications · doi:10.1135/cccc19960930 · Cited by 13 · see citing works

Stereoselective Synthesis of the Brassinolide Side Chain by the Use of a 5-Exo-α-Silyl Radical Cyclization - Protiodesilylation Sequence

Koreeda, M., & Wu, J. (1995) · Synlett · doi:10.1055/s-1995-5095 · Cited by 13 · see citing works

Synthesis of Analogues of Brassinosteroids with 5β-Cholanic Acid Skeleton

Gil, R. P., Martínez, C. S. P., & Manchado, F. C. (1998) · Synthetic Communications · doi:10.1080/00397919808004446 · Cited by 13 · see citing works

2,3,5-Tri-epi-brassinolide: preparation and biological activity in rice lamina inclination test

Seto, H., Fujioka, S., Koshino, H., Suenaga, T., Yoshida, S., Watanabe, T., & Takatsuto, S. (1999) · Phytochemistry · doi:10.1016/s0031-9422(99)00335-0 · Cited by 12 · see citing works

Synthesis of new Δ5-7-oxygenated and Δ5,7-unsaturated brassinosteroid analogs

Hellrung, B., Voigt, B., Schmidt, J., & Adam, G. (1997) · Steroids · doi:10.1016/s0039-128x(97)00008-1 · Cited by 11 · see citing works

Stereoselectivity of directed epoxidations of 22-hydroxy-Δ23-sterol side chains

Back, T. G., & Baron, D. L. (1996) · Canadian Journal of Chemistry · doi:10.1139/v96-208 · Cited by 10 · see citing works

17a-Oxa-17a-homobrassinosteroid Analogues

Kohout, L., Slavı́ková, B., & Strnad, M. (1998) · Collection of Czechoslovak Chemical Communications · doi:10.1135/cccc19980646 · Cited by 10 · see citing works

A C-B-A-D approach to brassinosteroids; Generation of the cis-anti-trans A-B-C ring system

Zoller, T., Uguen, D., Cian, A. D., Fischer, J., & Sablé, S. (1997) · Tetrahedron Letters · doi:10.1016/s0040-4039(97)00648-5 · Cited by 10 · see citing works

Conformational studies of two new brassinosteroid analogues with a 22,23-trans diol function

Drosihn, S., Porzel, A., Voigt, B., Brandt, W., Wagner, C., Merzweiler, K., & Adam, G. (1999) · Journal of the Chemical Society Perkin Transactions 2 · doi:10.1039/a807440b · Cited by 9 · see citing works

Improved Synthesis of Castasterone and Brassinolide†

Watanabe, T., Takatsuto, S., Fujioka, S., & Sakurai, A. (1997) · Journal of Chemical Research Synopses · doi:10.1039/a702805i · Cited by 9 · see citing works

New Synthesis of 28‐Homobrassinolide from Stigmasterol

Hazra, B. G., Kumar, T. P., & Joshi, P. L. (1997) · Liebigs Annalen · doi:10.1002/jlac.199719970536 · Cited by 8 · see citing works

Synthesis of new brassinosteroids with epoxy functions: The effect on the regioselectivity of the Baeyer-Villiger reaction

Brosa, C., & Miró, X. (1997) · Tetrahedron · doi:10.1016/s0040-4020(97)00716-3 · Cited by 8 · see citing works

Synthesis of two analogues of brassinolide, possible plant growth promoting steroids

Allevi, P., Longo, A., & Anastasia, M. (1999) · Tetrahedron · doi:10.1016/s0040-4020(99)00107-6 · Cited by 7 · see citing works

Generation of the trans-anti-trans A-B-C ring system of castasterone by intramolecular Diels-Alder reaction

Zöller, T., & Uguen, D. (1999) · Tetrahedron Letters · doi:10.1016/s0040-4039(99)01297-6 · Cited by 7 · see citing works

N-Benzoyl-N-methylandrostan-17β-amines; 20-Aza Analogues of Brassinolide

Slavı́ková, B., Kasal, A., & Kohout, L. (1998) · Collection of Czechoslovak Chemical Communications · doi:10.1135/cccc19980655 · Cited by 6 · see citing works

A new efficient procedure for the reduction of Δ7 ergostane derivatives

Brosa, C., & Rodríguez‐Santamarta, C. (1999) · Tetrahedron · doi:10.1016/s0040-4020(98)01191-0 · Cited by 5 · see citing works

Synthesis of Novel Azidocastasterone Derivative as a Potential Photoaffinity Label for the Brassinosteroid Receptor

Back, T. G., & Minksztym, K. (1999) · Synlett · doi:10.1055/s-1999-2585 · Cited by 4 · see citing works

Synthesis of a novel brassinosteroid type with an annelated dioxonane side chain

Lichtblau, D. A., Porzel, A., Schmidt, J. G., Voigt, B., & Adam, G. (1999) · Journal of the Chemical Society Perkin Transactions 1 · doi:10.1039/a807078d · Cited by 3 · see citing works

Synthesis of 5α,8α-ethanoergosta-2,6,22-triene-2′β-hydroxymethylene-1′β-carboxylic acid lactone, a key intermediate for the synthesis of a brassinolide analogue

Allevi, P., Longo, A., & Anastasia, M. (1999) · Chemistry and Physics of Lipids · doi:10.1016/s0009-3084(99)00100-0 · Cited by 2 · see citing works

Methods for construction of sidechain of brassinosteroids and application to syntheses of brassinosteroids

Jiang, B., Huang, L., Tian, W., & Zhou, W. (1996) · Studies in natural products chemistry · doi:10.1016/s1572-5995(96)80008-1 · Cited by 2 · see citing works

Axinellins A and B: New Proline-Containing Antiproliferative Cyclopeptides from the Vanuatu SpongeAxinella carteri

Randazzo, A., Dal Piaz, F., Orrù, S., Debitus, C., Roussakis, C., Pucci, P., & Gomez-Paloma, L. (1998) · European Journal of Organic Chemistry · doi:10.1002/(sici)1099-0690(199811)1998:11

Ecdysteroids

Lafont, R., Balducci, C., & Dinan, L. (2021) · Encyclopedia · doi:10.3390/encyclopedia1040096 · Cited by 49 · see citing works

Stereoselective syntheses of 20-epi cholanic acid derivatives from 16-dehydropregnenolone acetate

Shingate, B. B., Hazra, B. G., Pore, V. S., Gonnade, R. G., & Bhadbhade, M. M. (2007) · Tetrahedron · doi:10.1016/j.tet.2007.04.014 · Cited by 28 · see citing works

A Concise Account of Various Approaches for Stereoselective Construction of the C-20(H) Stereogenic Center in Steroid Side Chain

Shingate, B. B., & Hazra, B. G. (2014) · Chemical Reviews · doi:10.1021/cr4004083 · Cited by 26 · see citing works

Aza-annulation on the 16-dehydropregnenolone, via tandem intermolecular Aldol process and intramolecular Michael addition

Kumar, M., Rawat, P., Khan, M. F., Rawat, A. K., Srivastava, R., & Maurya, R. (2011) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/j.bmcl.2011.02.112 · Cited by 17 · see citing works

Increasing the amphiphilicity of an estradiol based steroid structure by Barbier-allylation – ring-closing metathesis – dihydroxylation sequence

Saloranta, T., Zupkó, I., Rahkila, J., Schneider, G., Woelfling, J., & Leino, R. P. (2011) · Steroids · doi:10.1016/j.steroids.2011.10.011 · Cited by 10 · see citing works

Synthesis and Biological Activity of Epoxy Analogues of 3-dehydroteasterone

Bernardo, Y., Alonso‐Becerra, E., Guerra, F. M., Massanet, G. M., Pérez-Martínez, C., & Coll-Manchado, F. (2007) · Journal of Chemical Research · doi:10.3184/030823407x210884 · Cited by 8 · see citing works

Synthesis and preliminary evaluation of dimeric-28-homobrassinosteroids for plant growth regulators

Phutdhawong, W. S., Ruensamran, W., & Phutdhawong, W. (2016) · Steroids · doi:10.1016/j.steroids.2016.08.016 · Cited by 5 · see citing works

Synthesis of (22R,23R)-2α,3α,22,23-Diepoxy-5α-Hydroxy-Stigmastan-6-One from Stigmasterol

Bernardo, Y., Alonso, E., Coll, F., Pérez, C., & Agüero, G. (2006) · Journal of Chemical Research · doi:10.3184/030823406776330783 · Cited by 5 · see citing works

Progress in the Chemical Synthesis of Brassinosteroids

Ковганко, Н. В., & Ананич, С. К. (2003) · ChemInform · doi:10.1002/chin.200310268 · Cited by 1 · see citing works

BindingDB Entry 50033151: Aza-annulation on the 16-dehydropregnenolone, via tandem intermolecular aldol process and intramolecular Michael addition.

BindingDB (2011) · UC San Diego · doi:10.7270/q2b858fh

Advances in the chemical synthesis of brassinosteroids

Ковганко, Н. В., & Ананич, С. К. (1997) · Chemistry of Natural Compounds · doi:10.1007/bf02282358 · Cited by 9 · see citing works

The synthesis of brassinosteroid

Zhou, W. (1989) · Pure and Applied Chemistry · doi:10.1351/pac198961030431 · Cited by 32 · see citing works

The synthesis of brassinosteroids, a new class of plant hormones

Лахвич, Ф. А., Khripach, V. A., & Zhabinskii, V. N. (1991) · Russian Chemical Reviews · doi:10.1070/rc1991v060n06abeh001100 · Cited by 21 · see citing works

Synthesis of brassinosteroids

Khripach, V. A. (1990) · Pure and Applied Chemistry · doi:10.1351/pac199062071319 · Cited by 17 · see citing works

Synthesis and Some Practical Aspects of Brassinosteroids

Khripach, V. A., Zhabinskii, V. N., & Litvinovskaya, R. P. (1991) · ACS symposium series · doi:10.1021/bk-1991-0474.ch005 · Cited by 8 · see citing works