SYNTHESIS OF VICINAL STEREOGENIC TERTIARY AND QUATERNARY CENTERS USING CHIRAL BICYCLIC LACTAMS AND DIASTEREOSELECTIVE PROTONATION - ASYMMETRIC-SYNTHESIS OF (+)-LAURENE

被引：21

作者：

SCHWARZ, JB ^{[1
]}

MEYERS, AI ^{[1
]}

机构：

[1] COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 20期

关键词：

D O I：

10.1021/jo00125a042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral bicyclic lactam 5, previously reported in the synthesis of(-)-alpha-cuparenone, was used to construct the more complex title compound 2. A mixture of cyclopentenones 8 and 9 was subjected to deprotonation/reprotonation to provide 8 in high diastereomeric excess. Transformation of 8 to the title compound was achieved by catalytic hydrogenation to 13, followed by methylenation with the Tebbe reagent.

引用

页码：6511 / 6514

页数：4

共 16 条

[1]

CHETTY GL, 1964, TETRAHEDRON LETT, P73

[2] ASYMMETRIC CONSTRUCTION OF QUATERNARY CARBONS FROM CHIRAL MALONATES - TOTAL SYNTHESES OF (+)-EPILAURENE AND (-)-ISOLAURENE [J].