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Synthesis 2009(3): 474-482
DOI: 10.1055/s-0028-1083321
DOI: 10.1055/s-0028-1083321
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Stereoselective Preparation of C1-C10 and C11-O14 Fragments of Narbonolide: Exploiting the Versatility of Thiazolidinethione Chiral Auxiliary [¹]
Weitere Informationen
Received
13 August 2008
Publikationsdatum:
12. Januar 2009 (online)
Publikationsverlauf
Publikationsdatum:
12. Januar 2009 (online)
![](https://www.thieme-connect.de/media/synthesis/200903/lookinside/thumbnails/10.1055-s-0028-1083321-1.jpg)
Abstract
An efficient stereoselective synthesis of the C1-C10 and C11-O14 fragments of narbonolide, have been accomplished by using a thiazolidinonethione as chiral auxiliary. The stereocenters at C2, C3, C4, C5, C8, and C9 in C1-C10 fragment and C12 and C13 in C11-C14 fragment were generated via asymmetric acyl-thiazolidinethione aldol reactions whereas the stereocenter at C6 was installed by means of Myers alkylation.
Key words
acyl-thiazolidinethione - aldol reaction - Crimmins protocol - Myers alkylation - Tebbe reaction
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