The Scripps Research Institute

Philippe G Nantermet

K C Nicolaou

Hiroaki Ueno

Rodney K Guy

Elias A Couladouros

Christopher F Claiborne

Kyriacos Costa Nicolaou

Erik J Sorensen

Zhen Yang

Jin-Jun Liu

Kc Nicolaou

Erik J Sorenson

A method for esterifying C13 deoxy taxoid intermediates employs three steps, i.e., oxygenation of the C13 deoxy taxoid intermediate to produce a C13 enone taxoid intermediate; reduction of the C13 enone to produce an alcohol; followed by esterification of the C13 alcohol. Key intermediates include C13 deoxy taxoids; C13 enone substituted taxoids; and C1-C2 cyclo carbonate esters of taxoids.

Transformations of taxol

Bioactive ABC taxoids accessible by convergent synthesis have an intact AB ring framework of taxol, including the C.sup.13 side chain, and an aromatic C ring which substitutes for the CD ring system found on native taxol. The aromatic C ring may be substituted or unsubstituted. MPT derivatives of ABC taxoids are also disclosed.

Taxoid synthesis

Transformations of taxol, baccatin III and of 10-deacetyl baccatin III provide access to novel taxol analogs and key intermediates thereto.

Access to taxol analogs

The total synthesis of taxol employs a convergent synthetic plan. The synthetic plan may also be employed to produce a large number of taxol analogs. Taxol analogs having skeletal extensions are inaccessible by modification of the natural product but are readily produced by employing the convergent synthetic plan herein.

Total synthesis of taxol and taxol analogs

Growing community of inventors

San Diego, CA, United States of America

Philippe G Nantermet