SYNTHESES OF NITRILE AND METHYL-ESTER CORRESPONDING TO (DL)-SARKOMYCIN AND OF RELATED-COMPOUNDS

被引：16

作者：

FROISSANT, J ^{[1
]}

VIDAL, J ^{[1
]}

GUIBEJAMPEL, E ^{[1
]}

HUET, F ^{[1
]}

机构：

[1] UNIV PARIS 11, CARBOCYCLES LAB, CNRS, UNITE 478, BATIMENT 420, F-91405 ORSAY, FRANCE

来源：

TETRAHEDRON | 1987年 / 43卷 / 02期

关键词：

D O I：

10.1016/S0040-4020(01)89959-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nitrile 6a and ester 12 corresponding to (dl)-sarkomycin, 6- and 7-membered rings analogue nitriles 6b, 6c, and 3-methyl substituted nitrile 6d were prepared. Conjugate addition of cyanotrimethyl silane to cyclic .alpha.-enones gave 3-trimethylsiloxy 2-cycloalkene carbonitriles. Their alkylation with chloromethyl phenyl sulfide followed by oxone oxidation to sulfones and sulfinic acid elimination on basic alumina led to .alpha.-methylene carbonyl compounds. Obtention of the ester 12 involved acetalization of 3-oxo 2-phenylthiomethyl cyclopentane carbonitrile, basic hydrolysis into acid, deacetalization, esterification, oxidation and elimination of sulfinic acid.

引用

页码：317 / 322

页数：6

共 24 条

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