Total Synthesis of (−)‐Cephalotaxine and (−)‐Homoharringtonine via Furan Oxidation–Transannular Mannich Cyclization,Angewandte Chemie International Edition

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Total Synthesis of (−)‐Cephalotaxine and (−)‐Homoharringtonine via Furan Oxidation–Transannular Mannich Cyclization
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2019-04-04 , DOI: 10.1002/anie.201902174
Xuan Ju ₁ , Christopher M. Beaudry ₁

Affiliation

Homoharringtonine and its congener cephalotaxine were synthesized. Oxidative ring‐opening of a furan unveils an amine‐tethered dicarbonyl, which undergoes spontaneous transannular Mannich cyclization. The cascade builds the full cephalotaxine substructure in a single operation in 60 % yield. A Noyori reduction enabled synthesis of the title compounds with excellent enantioselectivity (k_rel=278).

中文翻译：

通过呋喃氧化-环过曼尼希环化法合成（-）-头孢他辛和（-）-高灵碱

合成了人harringtonine及其同类物头孢他辛。呋喃的氧化性开环揭示了一种胺系的二羰基化合物，该胺基化合物会自发地经过环面Mannich环化。级联通过一次操作以60％的产率构建完整的头孢他辛亚结构。通过Noyori还原，能够以优异的对映选择性（k _rel＝ 278）合成标题化合物。

更新日期：2019-04-04

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