Indole diterpene synthetic studies. Total synthesis of (+)-nodulisporic acid F and construction of the heptacyclic cores of (+)-nodulisporic acids A and B and (-)-nodulisporic acid D

Amos B. Smith, Akin H. Davulcu, Shin Cho Young, Kazuyuki Ohmoto, László Kürti, Haruaki Ishiyama

Research output: Contribution to journalArticle

35 Scopus citations

Abstract

(Chemical Equation Presented) A first-generation strategy for construction of (+)-nodulisporic acids A (1) and B (2) is described. The strategy entails union of the eastern and western hemisphere subtargets via the indole synthesis protocol developed in our laboratory. Subsequent elaboration of rings E and F, however, revealed the considerable acid instability of the C(24) hydroxyl, thereby preventing further advancement. Nonetheless, preparation of the heptacyclic core of (+)-nodulisporic acids A and B, the total synthesis of (+)-nodulisporic acid F, the simplest member of the nodulisporic acid family, and elaboration of the heptacyclic core of (-)-nodulisporic acid D were achieved.

Original languageEnglish (US)
Pages (from-to)4596-4610
Number of pages15
JournalJournal of Organic Chemistry
Volume72
Issue number13
DOIs
StatePublished - Jun 22 2007

ASJC Scopus subject areas

  • Organic Chemistry

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