紫杉醇的生物合成研究。紫杉-4(20),11(12)-二烯-2α,5α-二醇的合成。

Studies on the biosynthesis of taxol. Synthesis Of taxa-4(20), 11(12)-diene-2alpha,5alpha-diol.

作者信息

Vázquez A, Williams R M

机构信息

Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.

出版信息

J Org Chem. 2000 Nov 17;65(23):7865-9. doi: 10.1021/jo005537+.

DOI:10.1021/jo005537+

PMID:11073592

Abstract

The synthesis of taxa-4(20),11(12)-diene-2alpha,5alpha-diol is described. An improved procedure for the intramolecular Diels-Alder cycloaddition previously reported in our synthesis of taxa-4(5), 11(12)-diene has been utilized to prepare a taxoid with oxygenation in the B and C rings. It has been established previously that taxa-4(20),11(12)-dien-5alpha-ol is the first oxygenated intermediate on the biosynthetic pathway to Taxol. Taxa-4(20), 11(12)-diene-2alpha,5alpha-diol (5), which has been observed in a biosynthetic conversion, is a potential candidate as the second oxygenated intermediate on the Taxol biosynthetic pathway, has been prepared to probe the intermediacy of this substance.

摘要

描述了紫杉-4(20),11(12)-二烯-2α,5α-二醇的合成。在我们之前合成紫杉-4(5),11(12)-二烯的过程中所报道的分子内狄尔斯-阿尔德环加成反应的改进方法，已被用于制备在B环和C环带有氧化官能团的紫杉烷类化合物。之前已经确定，紫杉-4(20),11(12)-二烯-5α-醇是紫杉醇生物合成途径中的首个氧化中间体。在生物合成转化过程中已观察到的紫杉-4(20),11(12)-二烯-2α,5α-二醇（5），作为紫杉醇生物合成途径中的第二个氧化中间体是一个潜在的候选物，已被制备出来以探究该物质的中间体性质。