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Synthesis 2005(7): 1183-1199
DOI: 10.1055/s-2005-865302
DOI: 10.1055/s-2005-865302
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart · New York
Synthesis of the C1-C17 Macrolactone of Tedanolide
Further Information
Received
30 November 2004
Publication Date:
23 March 2005 (online)
Publication History
Publication Date:
23 March 2005 (online)
Abstract
The vinylogous Mukaiyama aldol reaction is a useful method to build up complex polyketide structures. It is successfully employed in the synthesis of the C1-C17 macrolactone of tedanolide, a highly cytotoxic marine natural product. These studies present a practical approach toward the total synthesis of tedanolide; it is pursued using the appropriate C13-C23 segment that is introduced by a pivotal aldol reaction to join both hemispheres.
Key words
aldol reactions - macrocycles - Mitsunobu - tedanolide - total synthesis
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References
Hassfeld, J.; Kalesse, M. unpublished results.
45The C13 stereochemical assignment is based on analysis of the C12 1H NMR signals according to Ref. 39.