The total synthesis of (-)-crispatene.

Miller, Aubry K; Byun, Daniel H; Beaudry, Christopher M; Trauner, Dirk · Proc Natl Acad Sci U S A · 2004

basic_science · Level V

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Abstract

The total synthesis of the molluscan polypropionate (-)-crispatene is described. The synthesis features a palladium-catalyzed cross-coupling to establish a sensitive conjugated tetraene and its Lewis acid-catalyzed cycloisomerization to yield the bicyclo[3.1.0]hexene core of the natural product. The absolute configuration of (-)-crispatene and related molecules is established.

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