Synthesis of (±)-5-epi-citreoviral and (±)-citreoviral and the kinetic resolution of an allylic silane by a [3 + 2] annulation

Zhi H. Peng, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

(equation presented) The [3 + 2] annulation reaction of allylsilane 1 with an α-keto ester provided the highly substituted tetrahydrofuran 2 as a single diastereomer in high yield. The synthesis of (±)-5-epi-citreoviral and (±)-citreoviral has been accomplished with this annulation reaction as the key step. Using the pantolactone-derived α-keto ester, the allylsilane 1 has been resolved with high enantiomeric purity.

Original languageEnglish (US)
Pages (from-to)2945-2948
Number of pages4
JournalOrganic Letters
Volume4
Issue number17
DOIs
StatePublished - Aug 22 2002

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Silanes
silanes
esters
Esters
Kinetics
kinetics
synthesis
tetrahydrofuran
purity
allylsilane
citreoviral
pantolactone

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Synthesis of (±)-5-epi-citreoviral and (±)-citreoviral and the kinetic resolution of an allylic silane by a [3 + 2] annulation. / Peng, Zhi H.; Woerpel, Keith.

In: Organic Letters, Vol. 4, No. 17, 22.08.2002, p. 2945-2948.

Research output: Contribution to journalArticle

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