The DOI matches its Crossref record.
Synthesis, Absolute Configuration, and Enantiomeric Enrichment of a Cruciferous Oxindole Phytoalexin, (S)-(−)-Spirobrassinin, and Its Oxazoline Analog
Abstract
Stereochemical studies of a cruciferous oxindole phytoalexin, (S)-(-)-spirobrassinin [(-)-4], and its oxazoline analogue, spirooxazoline (11), were carried out. Racemic spirobrassinin [(+/-)-4] was synthesized by SOCl(2)- or MsCl-mediated cyclization of dioxibrassinin [(+/-)-8]. Treatment of (3-hydroxyoxindol-3-yl)methylammonium chloride [(+/-)-9] with CSCl(2) and subsequent methylation of the obtained spirooxazolidinethione (+/-)-10 afforded spirooxazoline [(+/-)-11]. Enantioresolution of (+/-)-4 and (+/-)-11 was achieved by derivatization with (S)-(-)-1-phenylethyl isocyanate (12), chromatographic separation of diastereomeric amides 13, 14 or 15, 16, and their cleavage with CH(3)ONa. Absolute configuration of the stereogenic center in natural (S)-(-)-4 was derived from the exciton, calculated via CD methods, and unequivocally confirmed by X-ray crystallographic analyses of 1-[1'S,4'R-(-)-camphanoyl] derivatives [(-)-19 and (-)-20] of (+)- and (-)-4. Novel enantiomeric enrichment phenomena of 4 and 11 were discovered during their chromatographic separations under achiral HPLC conditions. Screening of antifungal activity against the fungus Bipolaris leersiae revealed no significant dependence of this activity on absolute configuration.
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Cited by
Zhou, F., Liu, Y., & Zhou, J. (2010) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.201000161 · Cited by 1,252
Recent advances in organocatalytic methods for the synthesis of disubstituted 2- and 3-indolinones
Dalpozzo, R., Bartoli, G., & Bencivenni, G. (2012) · Chemical Society Reviews · doi:10.1039/c2cs35100e · Cited by 673
An overview of spirooxindole as a promising scaffold for novel drug discovery
Zhou, L.-M., Qu, R.-Y., & Yang, G.-F. (2020) · Expert Opinion on Drug Discovery · doi:10.1080/17460441.2020.1733526 · Cited by 316
Han, J., Soloshonok, V. A., Klika, K. D., Drabowicz, J., & Wzorek, A. (2018) · Chemical Society Reviews · doi:10.1039/c6cs00703a · Cited by 287
The self-disproportionation of enantiomers (SDE): a menace or an opportunity?
Han, J., Kitagawa, O., Wzorek, A., Klika, K. D., & Soloshonok, V. A. (2018) · Chemical Science · doi:10.1039/c7sc05138g · Cited by 121
The self-disproportionation of enantiomers (SDE) of amino acids and their derivatives
Han, J., Wzorek, A., Kwiatkowska, M., Soloshonok, V. A., & Klika, K. D. (2019) · Amino Acids · doi:10.1007/s00726-019-02729-y · Cited by 52
Metadata
- Authors
- Suchý, M., Kutschy, P., Monde, K., Goto, H., Harada, N., Takasugi, M., Dzurilla, M., & Balentová, E.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2001-04-27
- Volume
- 66
- Issue
- 11
- Pages
- 3940-3947
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2951027554
- Cited by
- 178
- References
- 0
- FWCI
- 2.71
- Type
- journal article
- Language
- en
- Open access
- closed
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