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On the construction of 2-substituted 1,4-diacetoxybutadiene moiety: application to the synthesis of (±)-caulerpenyne

✍ Scribed by Laurent Commeiras; Maurice Santelli; Jean-Luc Parrain

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 296 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)00235-1

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✦ Synopsis

The synthesis of 2-substituted 1,4-diacetoxybutadiene derivatives with a partial control of stereochemistry is described from two potentially precursor enals by a judicious choice of experimental conditions (Ac 2 O/DMAP in Et 3 N). These conditions have been successfully applied in the first total synthesis of caulerpenyne.

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