Enantioselective Synthesis of β-Necrodol and of 1-Epi-β-necrodol via Asymmetric 1,4-Addition and Magnesium-Ene Cyclization. Preliminary Communication

Von Oppolzer, Wolfgang; Schneider, Philippe

doi:10.1002/hlca.19860690805

Scientific article

English

Enantioselective Synthesis of β-Necrodol and of 1-Epi-β-necrodol via Asymmetric 1,4-Addition and Magnesium-Ene Cyclization. Preliminary Communication

ContributorsVon Oppolzer, Wolfgang; Schneider, Philippe

Published inHelvetica chimica acta, vol. 69, no. 8, p. 1817-1820

Publication date1986-12-10

First online date2004-10-25

Abstract

Enantiomerically pure β-necrodol (1) and its 1-epimer 16 have been synthesized starting from aldehyde 5. The two key steps are an asymmetric conjugate addtion/Mannich reaction tandem (10→12) and a type-II-magnesiumene cyclization/oxidation sequence (14→1 + 16).

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

VON OPPOLZER, Wolfgang, SCHNEIDER, Philippe. Enantioselective Synthesis of β-Necrodol and of 1-Epi-β-necrodol via Asymmetric 1,4-Addition and Magnesium-Ene Cyclization. Preliminary Communication. In: Helvetica chimica acta, 1986, vol. 69, n° 8, p. 1817–1820. doi: 10.1002/hlca.19860690805

Article (Published version)

Identifiers

PID : unige:155680
DOI : 10.1002/hlca.19860690805

Additional URL for this publicationhttps://onlinelibrary.wiley.com/doi/10.1002/hlca.19860690805

Journal ISSN0018-019X

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Enantioselective Synthesis of β-Necrodol and of 1-Epi-β-necrodol via Asymmetric 1,4-Addition and Magnesium-Ene Cyclization. Preliminary Communication

Enantiomerically pure β-necrodol (1) and its 1-epimer 16 have been synthesized starting from aldehyde 5. The two key steps are an asymmetric conjugate addtion/Mannich reaction tandem (10→12) and a type-II-magnesiumene cyclization/oxidation sequence (14→1 + 16).

Technical informations