Studies toward the synthesis of spirastrellolide A. Preparation of a C31-C47 model

Troy Lam, Nancy Totah

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The synthesis of a C31-C47 model of spirastrellolide A is reported. Key steps include an iron catalyzed cross coupling reaction to incorporate the linear side chain as a single unit, and the carbonyl ene reaction of an exocyclic enol ether to prepare the 5,6-spiroketal. A trans-ketalization from 5,6- to 6,6-spiroketal frameworks is used to facilitate stereochemical assignment.

Original languageEnglish (US)
Pages (from-to)3349-3352
Number of pages4
JournalTetrahedron Letters
Volume56
Issue number23
DOIs
StatePublished - May 25 2015

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Cross Reactions
Ether
Iron
spiroketal
spirastrellolide A

Keywords

  • Carbonyl ene reaction
  • Exocyclic enol ether
  • Iron catalyzed coupling reaction
  • Spirastrellolide
  • Spiroketals
  • trans-Ketalization

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Studies toward the synthesis of spirastrellolide A. Preparation of a C31-C47 model. / Lam, Troy; Totah, Nancy.

In: Tetrahedron Letters, Vol. 56, No. 23, 25.05.2015, p. 3349-3352.

Research output: Contribution to journalArticle

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AB - The synthesis of a C31-C47 model of spirastrellolide A is reported. Key steps include an iron catalyzed cross coupling reaction to incorporate the linear side chain as a single unit, and the carbonyl ene reaction of an exocyclic enol ether to prepare the 5,6-spiroketal. A trans-ketalization from 5,6- to 6,6-spiroketal frameworks is used to facilitate stereochemical assignment.

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