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Diastereoselective zirconocene-promoted bicyclization-carbonylation of allylically methyl-substituted enynes. Synthesis of (+)-iridomyrmecin

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
33
Issue
12
Identifiers
DOI: 10.1016/s0040-4039(00)91669-1

Abstract

Abstract Allylically methyl-substituted 1,6-heptenynes, such as 3-methyl-1,6-octenyne, can be diastereoselectivity converted to the corresponding bicyclic ketones, such as (5R, 6S)-2,6-dimethylbicyclo[3.3.0]oct-1-en-3-one readily convertible to (+)-iridomyrmecin, the observed diastereomeric excesses of the bicyclization reaction being >90%.

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