Synthesis of a Spirovetivane Synthon

George Pettit, Thomas B. Harvey

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

The spiravetivane sesquiterpenes are characterized by a Spiro [4.5]decane ring system. Illustrative are the essenti oil component β-betiv ne (1) and the antifungal metabolite lubimin (2).2 As part of a structural problem arising from our investigations of plant anticancer constituents1we developed a synthesis of the potential spirovetivane synthon 10. The very workable synthesis (5- > 10) of ketone 10 described below should prove useful in approaches to certair spirovetivanes with a 1,4 oxygen-carbon to spiro-carbon relationship. Initially efforts were directed at utilizing the Plattner3 malonic ester and Dieckmann cyclization4 approach (3- > 4) to ketone 7. The Singh4 route to ester 4.

Original languageEnglish (US)
Pages (from-to)167-177
Number of pages11
JournalSynthetic Communications
Volume11
Issue number3
DOIs
StatePublished - Jan 1 1981

ASJC Scopus subject areas

  • Organic Chemistry

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