AN ENANTIOSELECTIVE APPROACH TO THE TAXANES - DIRECT ACCESS TO FUNCTIONALIZED CIS-TRICYCLO[9.3.1.0(3,8)]PENTADECANES VIA ALPHA-HYDROXY KETONE AND WAGNER-MEERWEIN REARRANGEMENTS

被引：33

作者：

PAQUETTE, LA ^{[1
]}

ELMORE, SW ^{[1
]}

COMBRINK, KD ^{[1
]}

HICKEY, ER ^{[1
]}

ROGERS, RD ^{[1
]}

机构：

[1] NO ILLINOIS UNIV,DEPT CHEM,DE KALB,IL 60115

来源：

HELVETICA CHIMICA ACTA | 1992年 / 75卷 / 06期

关键词：

D O I：

10.1002/hlca.19920750603

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The feasibility of the titled reactions for the rapid, enantioselective synthesis of cis-tricyclo[9.3.1.0(3,8)]pentadecane precursors to taxusin and taxol has been examined. The catalysts most well suited to inducing the appropriate 1,2-shifts have been identified. To a great extent, the rearrangement products are formed as a direct consequence of appropriate structural features (kinetic phenomenon) and strain minimization (thermodynamic driving force). Complementary MM2 calculations of the global minimum in each series provided indications that were completely in line with the experimental observations. Sophisticated NMR studies and X-ray crystallographic determinations were coordinated to remove any ambiguity of product structure and solid-state conformation.

引用

页码：1755 / 1771

页数：17

共 30 条

[1] CONFORMATIONAL-ANALYSIS .130. MM2 - HYDROCARBON FORCE-FIELD UTILIZING V1 AND V2 TORSIONAL TERMS [J].