jo005537+_si_001.pdf (451.88 kB)
Studies on the Biosynthesis of Taxol. Synthesis of Taxa-4(20),11(12)-diene-2α,5α-diol
journal contribution
posted on 2000-10-21, 00:00 authored by Alfredo Vázquez, Robert M. WilliamsThe synthesis of taxa-4(20),11(12)-diene-2α,5α-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-5α-ol is the first oxygenated intermediate on the
biosynthetic pathway to Taxol. Taxa-4(20),11(12)-diene-2α,5α-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.