Isonitriles from the Blue-Green Alga Scytonema mirabile

Shmuel Carmeli, Richard E. Moore, Gregory M.L. Patterson, Yuji Mori, Makoto Suzuki

Research output: Contribution to journalArticlepeer-review

Abstract

An aerial form of Scytonema mirabile (Dillwyn) Bornet, designated strain number BY-8-1, has been found to contain six novel isonitriles, viz. mirabilene isonitriles A-F (7—12), which are mildly cytotoxic and antimicrobial. The gross structures of 7–12 were determined by detailed spectral analysis. The relative and absolute stereochemistry of 7–12 were solved by chemical degradation and direct comparison of degradation products with synthetic samples; mirabilene-A isonitrile (7), for example, was degraded to methyl (3R,5/?,7S,9S)-3,5,7,9-tetrameth-oxy-10-oxoundecanal (15) and isopropyl (S)-3-trifluoroacetamidobutyrate (14), which indicated that the absolute configurations of C-4, C-6, C-8, C-10, and C-16 in 7 were all S.

Original languageEnglish
Pages (from-to)4431-4438
Number of pages8
JournalJournal of Organic Chemistry
Volume55
Issue number14
DOIs
StatePublished - 1990
Externally publishedYes

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