Tetrahedron Letters p. 2325 - 2328 (1997)
Update date:2022-08-03
Topics:
Barrero, Alejandro F.
Alvarez-Manzaneda, Enrique J.
Chahboun, Rachid
The first enantiospecific synthesis of the antitumor and cholesteryl ester transfer protein (CETP) inhibitor (+)-puupehenone (19) from (-)-sclareol (10) and protocatechualdehyde (4) is described. The key steps of the reaction sequence are the organoselenium-induced cyclization of the mixture of regioisomers 15a-b to give 16 and 17, with complete diastereoselectivity, and the simultaneous removal of benzyl and phenylselenyl groups of 16 and 17 by treating with Raney Ni.
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