Acyclic stereocontrol through the dianionic Claisen rearrangement of β-hydroxy esters: Synthesis of (±)-botryodiplodin

Mark J. Kurth, Chan Mo Yu

Research output: Contribution to journalArticle

40 Scopus citations

Abstract

Dianionic Claisen rearrangements of (E)- and (Z)-butenyl β-hydroxy esters afford moderate stereoselection in the construction of highly functionalized acyclic systems. The reaction proceeds with remote stereocontrol and the resulting products display three contiguous chiral centers, C(α) and C(β′) stereocenters being established in the rearrangement (cf. 1z → 3b). Experiments are described which unambiguously establish that each dianionic Claisen proceeds with excellent diastereoface selectivity [C(α),C(β) stereocontrol] and moderate chair/boat selectivity [C(α),C(β′) stereocontrol]. Application of this Claisen protocol to a synthesis of the mycotoxin botryodiplodin is also described (1z → 8b).

Original languageEnglish (US)
Pages (from-to)1840-1845
Number of pages6
JournalJournal of Organic Chemistry
Volume50
Issue number11
StatePublished - 1985

ASJC Scopus subject areas

  • Organic Chemistry

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