ENANTIOSELECTIVE TOTAL SYNTHESES OF PUMILIOTOXIN-B AND PUMILIOTOXIN-251D - A GENERAL ENTRY TO THE PUMILIOTOXIN-A ALKALOIDS VIA STEREOSPECIFIC IMINIUM ION VINYLSILANE CYCLIZATIONS
ENANTIOSELECTIVE TOTAL SYNTHESES OF PUMILIOTOXIN-B AND PUMILIOTOXIN-251D - A GENERAL ENTRY TO THE PUMILIOTOXIN-A ALKALOIDS VIA STEREOSPECIFIC IMINIUM ION VINYLSILANE CYCLIZATIONS
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DOI：
10.1021/ja00327a022
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发表时间：
1984-01-01
影响因子：
15
通讯作者：
ITO, F
中科院分区：
文献类型：
--
作者：
OVERMAN, LE;BELL, KL;ITO, F
报道了从巴拿马毒蛙Dendrobates Pumilio中首次分离得到的Pumiliooxin B(1)和Pumiliooxin251D(3)的对映选择性全合成。肉毒杆菌毒素B的合成第一次明确地确立了这种潜在的重要心脏药物的完整立体结构。关键的合成策略是使用亚胺离子-乙烯基硅烷环化来形成中氮肼环体系，并建立亚烷基侧链的Z立体化学。
Enantioselective total syntheses of pumiliotoxin B (1) and pumiliotoxin 251D (3) [first isolated from the Panamanian poison frog Dendrobates pumilio] are reported. The synthesis of pumiliotoxin B unambiguously establishes, for the first time, the complete stereostructure of this potentially important cardiac agent. The key synthetic tactic is the use of an iminium ion-vinylsilane cyclization to both form the indolizidine ring system and establish the Z stereochemistry of the alkylidene side chain.