Stereospecific palladium(0)-catalyzed reduction of 2-cyclobutylidenepropyl esters.: A versatile preparation of diastereomeric monoterpenoids:: (±)-fragranol and (±)-grandisol

被引：24

作者：

Bernard, AM

Frongia, A

Secci, F

Delogu, G

Ollivier, J

Piras, PP

Salaün, J

机构：

[1] Univ Cagliari, Dipartimento Sci Chim, Cagliari, Italy

[2] CNR, Sez Sassari, Ist Chim Biomol, I-07040 Sassari, Italy

[3] Univ Paris 11, Inst Chim Mol Orsay, CNRS, Lab Carbocycles,UMR 8615, F-91405 Orsay, France

来源：

TETRAHEDRON | 2003年 / 59卷 / 47期

关键词：

palladium and compounds; stereospecificity; cyclobutanes; natural products;

D O I：

10.1016/j.tet.2003.09.074

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mixtures of (E and Z)-2-cyclobutylidenepropyl sulfonates, readily available from alpha,alpha-disubstituted cyclobutanones arising from suitable cyclopropane derivatives ring expansion, underwent regioselective and stereospecific reduction by formate anion to offer, through pi-1, 1-trimethyleneallylpalladium complexes formed upon treatment with palladium(O), a new and convenient entry to the diastereomeric four-membered ring monoterpenoids (+/-)-fragranol and (+/-)-grandisol. (C) 2003 Elsevier Ltd. All rights reserved.

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页码：9433 / 9440

页数：8

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