Studies on taxol biosynthesis. Preparation of 5α-acetoxytaxa-4(20),11-dien-2α,10β-diol derivatives by deoxygenation of a taxadiene tetra-acetate obtained from Japanese yew

The early stages of taxol biosynthesis: An interim report on the synthesis and identification of early pathway metabolites

“…In addition, we found that conversion of taxusin into the corresponding tetraol, followed by protection of the 9,10-diol unit as its cyclic carbonate proved advantageous and reproducible. 82 …”

“…In addition, we found that conversion of taxusin into the corresponding tetraol, followed by protection of the 9,10-diol unit as its cyclic carbonate proved advantageous and reproducible. 82 microsomal enzymes have been fully characterized, and the respective cytochrome P450 genes have been cloned. 83,84 The enzymes, originally obtained from T. cuspidata, 83 show conversion of taxa-4(20),11(12)-diene-5a-ol (26) (as well as its C20 tritium labeled isotope), to the subsequent diols, but 10bhydroxylase prefers taxa-4(20),11(12)-diene-5a-acetate (27) (as well as its C20 tritium labeled isotope) as substrate and 13ahydroxylase prefers taxa-4(20),11(12)-diene-5a-ol (26) (Scheme 17).…”

Relationship between the Structures of Taxane Derivatives and Their Microtubule Polymerization Activity

“…Taxanes 1 (Taxinine), 2 (taxusin), 3 (taxinine M), 17,18) 4, 5 (Shi and Kiyota, manuscripts in preparation), and 6 19,20) were isolated from the Japanese yew Taxus cuspidata. Taxanes 7-10, 21,22) 11, and 12 22) were prepared by our methods. The synthesis of 13-18 is described in Supporting Information.…”

Chemical Studies on Taxus cuspidata

“…Barton deoxygenation of a protected derivative of 2a,5a,10b-triacetoxy-14b-(2-methyl)-butyryloxytaxa-4(20),11-diene lead to 5a-acetoxytaxa-4(20),11-dien-2a,10b-diol and the latter is a promising candidate as a biosynthetic pathway triol in taxol biosynthesis. Horiguchi reported some experiments to probe further intermediate steps in the biosynthesis of taxol [96].…”