Studies on the biosynthesis of taxol. Synthesis Of taxa-4(20), 11(12)-diene-2alpha,5alpha-diol.
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.
Vázquez
A
A
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Williams
R M
RM
D000972:Antineoplastic Agents, Phytogenic / Q000096:biosynthesis*; D017239:Paclitaxel / Q000096:biosynthesis*
D000972:Antineoplastic Agents, Phytogenic; D017239:Paclitaxel