Synthesis of (+)-sch 642305 by a biomimetic transannular Michael reaction.

ABSTRACT: [reaction: see text] The synthesis of (+)-Sch 642305 (1) has been completed in 17 steps in 1.6% overall yield. Transannular Michael reaction of 2b with NaH in THF provided cyclohexenone 23 stereospecifically. Heating 23 in TFA/CDCl(3) provided a 3:1 equilibrium mixture of 23 and 25, which was hydrolyzed to give (+)-6-epi-Sch 642305 (24) and (+)-Sch 642305 (1), respectively.

SUBMITTER: Snider BB 

PROVIDER: S-EPMC2543932 | biostudies-literature | 2006 Mar

REPOSITORIES: biostudies-literature