Stereoselective synthesis of (all-Z)-hentriaconta-3,6,9,12,15,19,22,25,28-nonaene

Organic & Biomolecular Chemistry
Liudmila FilippovaYngve Stenstrøm

Abstract

Several microorganisms produce small quantities of polyunsaturated hydrocarbons and such natural products are of interest. Starting from the ethyl ester of eicosapentaenoic acid, the total synthesis of the natural product (all-Z)-hentriaconta-3,6,9,12,15,19,22,25,28-nonaene has been achieved in eight steps and 15% overall yield. The synthesis is based on a stereoselective Wittig reaction and confirms the all-Z-configuration of the nine double bonds in this highly unsaturated natural product.

References

Jun 1, 1983·Proceedings of the National Academy of Sciences of the United States of America·E J CoreyJ R Cashman
Apr 29, 1999·Microbiology·N J Russell, D S Nichols
Apr 27, 2010·Applied and Environmental Microbiology·David J SukovichLawrence P Wackett
Apr 27, 2010·Applied and Environmental Microbiology·David J SukovichLawrence P Wackett
Jun 10, 2011·Journal of Basic Microbiology·Taro Motoigi, Hidetoshi Okuyama
Mar 26, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Anne Marie LangseterLars Skattebøl
Aug 12, 2014·Progress in Lipid Research·Yangmin GongFenghong Huang
Dec 3, 2014·Current Opinion in Biotechnology·Sang Yup LeeSeungwoo Cheon

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Citations

Feb 18, 2020·Bioorganic Chemistry·Maria K PangopoulosTrond Vidar Hansen

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