Organic letters

Enantioselective Synthesis of a trans-7, 8-Dimethoxycalamenene

S Werle, T Fey, JM Neudörfl, HG Schmalz

Index: Werle, Susen; Fey, Thorsten; Neudoerfl, Joerg M.; Schmalz, Hans-Guenther Organic Letters, 2007 , vol. 9, # 18 p. 3555 - 3558

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Citation Number: 37

Abstract

trans-7, 8-Dimethoxy-11, 12-dehydrocalamenene, a projected intermediate for the total synthesis of marine serrulatane and amphilectane diterpenes, was efficiently synthesized. Starting from a styrene, asymmetric Rh-catalyzed hydroboration using a novel chiral P, P- bidentate ligand afforded an organoboron intermediate (93% ee) which was directly used for CC bond formation (double homologation, Suzuki coupling). The 1, 4-trans-disubstituted ...