The total synthesis of (+)-migrastatin

Christoph Gaul, Jon T Njardarson, Samuel J. Danishefsky

Research output: Contribution to journalArticle

89 Citations (Scopus)

Abstract

The first total synthesis of (+)-migrastatin, a macrolide natural product with interesting antimetastatic properties, has been accomplished. Our concise and flexible approach utilizes a Lewis acid-catalyzed diene aldehyde condensation to install the three contiguous stereocenters and the trisubstituted (Z)-alkene of migrastatin. Construction of the two remaining stereocenters and incorporation of the glutarimide-containing side chain have been achieved via an anti-selective aldol reaction, followed by a Horner-Wadsworth-Emmons olefination. Finally, the assembly of the macrocycle has been realized by a highly (E)-selective ring-closing metathesis.

Original languageEnglish (US)
Pages (from-to)6042-6043
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number20
DOIs
StatePublished - May 21 2003
Externally publishedYes

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Aldehydes
Olefins
Condensation
Lewis Acids
Acids
Macrolides
Alkenes
Biological Products
migrastatin
3-hydroxybutanal
glutarimide

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

The total synthesis of (+)-migrastatin. / Gaul, Christoph; Njardarson, Jon T; Danishefsky, Samuel J.

In: Journal of the American Chemical Society, Vol. 125, No. 20, 21.05.2003, p. 6042-6043.

Research output: Contribution to journalArticle

Gaul, Christoph ; Njardarson, Jon T ; Danishefsky, Samuel J. / The total synthesis of (+)-migrastatin. In: Journal of the American Chemical Society. 2003 ; Vol. 125, No. 20. pp. 6042-6043.
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