An Enantiospecific Synthesis of Solenopsin A

Jefford, Charles; Wang, Jian Bo

doi:10.1016/S0040-4039(00)60479-3

Scientific article

Letter

English

An Enantiospecific Synthesis of Solenopsin A

ContributorsJefford, Charles; Wang, Jian Bo

Published inTetrahedron Letters, vol. 34, no. 18, p. 2911-2914

Publication date1993

Abstract

Enantiomerically pure solenopsin A (1) was prepared in 11 steps from L-aspartic acid (3) in an overall yield of 17%. 6R-(N-tosylamino)heptadecan-2-one (8), prepared from 3, underwent cyclization on acid catalysis to N-tosylamino-2,3-dehydro-2-methyl-6R-undecylpiperidine (9), which on reduction and deprotection gave 1.

Keywords

2.6-Dialkylpiperidine
Innate chirality
Hydride reduction
Iminium cation

Affiliation entities

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

Funding

Swiss National Science Foundation - 20-32166.91

Citation (ISO format)

JEFFORD, Charles, WANG, Jian Bo. An Enantiospecific Synthesis of Solenopsin A. In: Tetrahedron Letters, 1993, vol. 34, n° 18, p. 2911–2914. doi: 10.1016/S0040-4039(00)60479-3

Article (Published version)

Identifiers

PID : unige:151889
DOI : 10.1016/S0040-4039(00)60479-3

Additional URL for this publicationhttps://linkinghub.elsevier.com/retrieve/pii/S0040403900604793

Journal ISSN0040-4039

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An Enantiospecific Synthesis of Solenopsin A

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