Stereoselective synthesis of anamarine

A stereoselective synthesis of the naturally occurring, α,β-unsaturated lactone anamarine is described. The key step was a highly stereoselective aldol reaction of a protected erythrulose derivative with a chiral aldehyde. Another relevant step was an asymmetric aldehyde allylation with a chiral all...

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Bibliographic Details
Published in:Tetrahedron 2004-03, Vol.60 (13), p.2979-2985
Main Authors: Dı́az-Oltra, Santiago, Murga, Juan, Falomir, Eva, Carda, Miguel, Marco, J.Alberto
Format: Article
Language:English
Subjects:
Anamarine
Asymmetric allylboration
Boron aldol reactions
Erythrulose
Ring-closing metathesis
Stereoselectivity
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Summary:A stereoselective synthesis of the naturally occurring, α,β-unsaturated lactone anamarine is described. The key step was a highly stereoselective aldol reaction of a protected erythrulose derivative with a chiral aldehyde. Another relevant step was an asymmetric aldehyde allylation with a chiral allylborane. The lactone ring was made by means of a ring-closing metathesis. The naturally occurring, cytotoxic lactone (+)-anamarine has been synthesized in a completely stereoselective way. The aldol reaction of a suitably protected l-erythrulose derivative with a ( S)-lactaldehyde derivative was the key step of the synthesis. An asymmetric allylation and a ring-closing metathesis were further relevant steps.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.02.003