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Sterospecific Syntheses and Spectroscopic Properties of Isomeric 2,4,6,8‐Undecatetraenes. New Hydrocarbons from the Marine Brown Alga Giffordia mitchellae. Part IV.
Abstract
Giffordene (=(2 Z,4 Z,6 E,8 Z)‐2,4,6,8‐undecatetraene; 9f) and five steroisomers are new C 11 H 16 hydrocarbons from the marine brown alga Giffordia mitchellae. Their synthesis is based on non‐stereoselective Wittig reactions of (E)‐2‐alkenals with appropriate acetylenic phosphoranes and subsequent chromatographic separation of the resulting (E/Z)‐pairs. The uniform enynes (>98% purity) are then stereospecifically reduced to (Z)‐alkenes with Zn(Cu/Ag) in aq. MeOH at r.t. 13 C‐ and 1 H‐NMR data of the new tetraenes are presented. Biosynthetically, giffordene (9f) originates from dodeca‐3,6,9‐trienoic acid via an unstable (3 Z,5 Z,8 Z)‐1,3,5,8,‐undecatetraene followed by a thermally allowed antarafacial 1,7‐sigmatropic hydrogen shift to the (2 Z,4 Z,6 E,8 Z)‐isomer 9f.
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Cited by
Oger, C., Balas, L., Durand, T., & Galano, J.-M. (2013) · Chemical Reviews · doi:10.1021/cr3001753 · Cited by 396
Petasis, N. A., Yang, R., Winkler, J. W., Zhu, M., Uddin, J., Bazan, N. G., & Serhan, C. N. (2012) · Tetrahedron Letters · doi:10.1016/j.tetlet.2012.01.032 · Cited by 45
New Transmembrane Polyene Bolaamphiphiles as Fluorescent Probes in Lipid Bilayers
Quesada, E., Acuña, A. U., & Amat‐Guerri, F. (2001) · Angewandte Chemie International Edition · doi:10.1002/1521-3773(20010601)40:11<2095::aid-anie2095>3.0.co;2-i · Cited by 34
Metadata
- Authors
- Boland, W., Schroer, N., Sieler, C., & Feigel, M.
- Venue
- Helvetica Chimica Acta
- Publisher
- Wiley
- Published
- 1987-07-08
- Volume
- 70
- Issue
- 4
- Pages
- 1025-1040
- ISSN
- 0018-019X (ISSN-L)
- 1522-2675
- OpenAlex
- W1963717084
- Cited by
- 210
- References
- 0
- FWCI
- 7.12
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Sterospecific Syntheses and Spectroscopic Properties of Isomeric 2,4,6,8‐Undecatetraenes. New Hydrocarbons from the Marine Brown Alga Giffordia mitchellae. Part IV. https://app.cochat.ai/papers/10.1002/hlca.19870700415
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- Boland, W., Schroer, N., Sieler, C., & Feigel, M. (1987). Sterospecific Syntheses and Spectroscopic Properties of Isomeric 2,4,6,8‐Undecatetraenes. New Hydrocarbons from the Marine Brown Alga Giffordia mitchellae. Part IV. Helvetica Chimica Acta. https://doi.org/10.1002/hlca.19870700415
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