Francis G. Fang

Convergent catalytic asymmetric synthesis of camptothecin analog GI147211C

The topoisomerase I inhibitor GI147211C (4) was discovered at Glaxo Wellcome and shown to have promising anti-cancer properties. In order to fully assess the clinical potential of 4, an improved synthesis of the drug substance was required. Herein is described a convergent catalytic asymmetric synthesis of 4 which utilizes as key steps, two Heck reactions, a Sharpless asymmetric dihydroxylation reaction, and a Mitsunobu reaction. A 2-chloroquinoline is shown to be a viable substrate for the final Heck reaction to generate the camptothecin nucleus.

Synthesis of a B-homo-6-azaandrost-4-ene-3-one as a novel steroidal 5α-reductase inhibitor

Abstract The preparation of a B-ring homologated analog of 17β-N,N-diethylcarboxy-6-azaandrost-4-ene-3-one, a potent inhibitor of type 2 steroidal 5α-reductase, is described.

Efficient construction of 6-azasteroids: dual inhibitors of steroidal 5α-reductase

A new route to 17 beta-substituted-6-azaandrost-4-en-3-ones, potent dual inhibitors of type 1 and 2 steroidal 5 alpha-reductase, is described.