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Synlett 2007(15): 2351-2354
DOI: 10.1055/s-2007-985601
DOI: 10.1055/s-2007-985601
LETTER
© Georg Thieme Verlag Stuttgart · New York
Stereoselective Synthesis of the C(53)-C(67) Polyene Fragment of Amphidinol 3
Further Information
Received
4 June 2007
Publication Date:
22 August 2007 (online)
Publication History
Publication Date:
22 August 2007 (online)
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Abstract
A stereoselective synthesis of the polyene fragment C(53)-C(67) of amphidinol 3 is described using a sequence of reduction, benzoylation, and reductive elimination for the stereospecific preparation of the polyene motif as key steps starting from acetylenic precursors.
Key words
amphidinol 3 - natural products - total synthesis - reductive elimination - addition reactions
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References and Notes
The all-trans configuration of the triene moiety was confirmed by performing 1H NMR irradiation experiments on the corresponding symmetrical diol, which is easily available by deprotection of the silyl groups starting from diol 14. The analysis of 1H-decoupled NMR spectra resulted in a coupling constant consistent with E-olefins (J = 14.1 Hz).