TANDEM MANGANESE(III)-BASED OXIDATIVE FREE-RADICAL CYCLIZATIONS TERMINATED BY ADDITION TO FURANS. FORMAL SYNTHESIS OF 15-ACETOXYPALLESCENSIN-A
作者:Barry B. Snider、Sean M O'Hare
DOI:10.1081/scc-100108225
日期:2001.1.1
Reaction of β-keto ester 12 with 2 equiv. of Mn(OAc)32H2O in KOAc-buffered MeOH followed by acidic workup afforded 51% of tricyclic furan 14 indicating that oxidative cyclizations can be terminated by addition to furans. Reduction of 14 with LAH provided 7, completing a five-step formal synthesis of 15-acetoxypallescensin-A.
β-酮酯 12 与 2 当量的反应。Mn(OAc)32H2O 在 KOAc 缓冲的 MeOH 中,然后进行酸处理,得到 51% 的三环呋喃 14,表明氧化环化可以通过加入呋喃来终止。用 LAH 还原 14 提供 7,完成 15-乙酰氧基pallescensin-A 的五步正式合成。