Enantioselective Synthesis of a trans-7,8-Dimethoxycalamenene

被引：46

作者：

Werle, Susen ^{[1
]}

Fey, Thorsten ^{[1
]}

Neudorfl, Jorg M. ^{[1
]}

Schmalz, Hans-Gunther ^{[1
]}

机构：

[1] Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 18期

关键词：

D O I：

10.1021/ol071228v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 C-C bond formation (double homologation, Suzuki coupling). The 1,4-trans-disubstituted tetralin skeleton was selectively formed by a Friedel-Crafts-type cationic cyclization under strictly aprotic conditions (Me2AlCl) to suppress a remarkable proton-catalyzed disproportionation via diastereoselective hydride transfer.

引用

页码：3555 / 3558

页数：4

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