Development of a scalable synthesis of a common eastern tricyclic lactone for construction of the nodulisporic acids

Amos B. Smith, László Kürti, Akin H. Davulcu, Young Shin Cho

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

A scalable, second-generation synthesis of the densely functionalized eastern tricyclic lactone (+)-6, a common intermediate, for construction of the nodulisporic acids has been achieved. Modifications to the first-generation route now permit access to (+)-6 in 17 steps with an overall 16.5% yield. Key carbon-carbon bond constructions include a Kirk-Petrow (phenylthio)methylation, a Sc(OTf)3 catalyzed hydroxymethylation, a Stille carbonylation, and a Koga three-component, conjugate addition- alkylation sequence.

Original languageEnglish (US)
Pages (from-to)19-24
Number of pages6
JournalOrganic Process Research and Development
Volume11
Issue number1
DOIs
StatePublished - Jan 2007

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Lactones
Carbon
Carbonylation
acids
Acids
methylation
Methylation
carbon
alkylation
Alkylation
synthesis
routes
scandium triflate

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry

Cite this

Development of a scalable synthesis of a common eastern tricyclic lactone for construction of the nodulisporic acids. / Smith, Amos B.; Kürti, László; Davulcu, Akin H.; Cho, Young Shin.

In: Organic Process Research and Development, Vol. 11, No. 1, 01.2007, p. 19-24.

Research output: Contribution to journalArticle

Smith, Amos B. ; Kürti, László ; Davulcu, Akin H. ; Cho, Young Shin. / Development of a scalable synthesis of a common eastern tricyclic lactone for construction of the nodulisporic acids. In: Organic Process Research and Development. 2007 ; Vol. 11, No. 1. pp. 19-24.
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