The total synthesis of (-)-crispatene.
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.
Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, CA 94720-1460, USA.
Aubry K
AK
Miller
Daniel H
DH
Byun
Christopher M
CM
Beaudry
Dirk
D
Trauner
D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods; D015394:Molecular Structure; D008974:Mollusca / Q000737:chemistry; D013237:Stereoisomerism
D001688:Biological Products