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 Citations (Scopus)

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

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Diterpenes
Acids
Hydroxyl Radical
nodulisporic acid F
nodulisporic acid D
indole
nodulisporic acid A

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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

In: Journal of Organic Chemistry, Vol. 72, No. 13, 22.06.2007, p. 4596-4610.

Research output: Contribution to journalArticle

Smith, Amos B. ; Davulcu, Akin H. ; Young, Shin Cho ; Ohmoto, Kazuyuki ; Kürti, László ; Ishiyama, Haruaki. / 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. In: Journal of Organic Chemistry. 2007 ; Vol. 72, No. 13. pp. 4596-4610.
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AU - Davulcu, Akin H.

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AU - Ohmoto, Kazuyuki

AU - Kürti, László

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