Synthesis of (+)-Sch 642305 by a Biomimetic Transannular Michael Reaction

Autor: B. Snider, Barry, Zhou, Jingye
Zdroj: Organic Letters; March 2006, Vol. 8 Issue: 7 p1283-1286, 4p
Abstrakt: The synthesis of (+)-Sch 642305 (1) has been completed in 17 steps in 1.6% overall yield. Transannular Michael reaction of 0 with NaH in THF provided cyclohexenone 23 stereospecifically. Heating 23 in TFA/CDCl3 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.
Databáze: Supplemental Index