Asymmetric total synthesis of ent-Tetrahydrolipstatin from an epoxy alkenol

Hyemi Kim, Kyeonghwan Choi, Jinsung Tae

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

A highly efficient asymmetric total synthesis of ent-tetrahydrolipstatin (THL) was accomplished from the known epoxy alkenol. The β-lactone portion of THL was synthesized by the epoxide opening with cyanide and stereoselective enolate alkylation method. The side chain was introduced by cross metathesis of the alkene part with 1-decene. Coupling with a protected leucine completed the synthesis of ent-tetrahydrolipstatin.

Original languageEnglish
Pages (from-to)1832-1834
Number of pages3
JournalSynlett
Volume23
Issue number12
DOIs
Publication statusPublished - 2012 Jul 6

Fingerprint

Epoxy Compounds
Alkylation
Cyanides
Alkenes
Lactones
Leucine
orlistat

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Kim, Hyemi ; Choi, Kyeonghwan ; Tae, Jinsung. / Asymmetric total synthesis of ent-Tetrahydrolipstatin from an epoxy alkenol. In: Synlett. 2012 ; Vol. 23, No. 12. pp. 1832-1834.
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Asymmetric total synthesis of ent-Tetrahydrolipstatin from an epoxy alkenol. / Kim, Hyemi; Choi, Kyeonghwan; Tae, Jinsung.

In: Synlett, Vol. 23, No. 12, 06.07.2012, p. 1832-1834.

Research output: Contribution to journalArticle

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