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An enantiospecific synthesis of (+)-methyl epijasmonate and (−)-methyl cucurbate from L-glutamic acid

✍ Scribed by Tarun K. Sarkar; Bireswar Mukherjee; Sunil K. Ghosh

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
903 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

An enantiospeci!ic route to jasmonoid natural products, (+) -methyl epijasmonate and (-) -methyl cucmbate from L-glutamic acid is reported. The key step is a 5-(3,4) ene cyclization of a fmxtionahzed 14diene as chiron. which sets up three chin11 centres with a high degree of diastereoselectivity.

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✍ A. Duréault; F. Carreaux; J.C. Depezay 📂 Article 📅 1989 🏛 Elsevier Science 🌐 French ⚖ 178 KB

Polyoxamic acid , 2-amino-2-deoxy-L-xylonic acid, is synthetized by thiophenoxide opening of a five-carbon chiral hydroxylated aziridine easily derived from L-arabinose. The formation of the carboxy group resulted lrom a Pummerer reaction. Polyoxins belong to a group of antifungal antibiotics produc