A conjugate addition/dipolar-cycloaddition cascade sequence for the synthesis of (±)-cylindricine C

被引：20
作者：
Flick, Andrew C. [1 ]
Arevalo Caballero, Maria Jose [1 ]
Padwa, Albert [1 ]
机构：
[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA
来源：
TETRAHEDRON | 2010年 / 66卷 / 21期
基金：
美国国家科学基金会;
关键词：
Alkaloid; Cylindricine C; 2,3-Bis(phenylsulfonyl)-1,3-butadiene; Oxime; Nitrone; Intramolecular dipolar cycloaddition; ASCIDIAN CLAVELINA-CYLINDRICA; MARINE ALKALOID LEPADIFORMINE; MERCURIC ACETATE OXIDATION; DIPOLAR CYCLOADDITION; UNSATURATED AMINES; ASYMMETRIC-SYNTHESIS; NATURAL ENANTIOMER; TERMINAL OLEFINS; (+)-CYLINDRICINE-C; (-)-LEPADIFORMINE;
D O I：
10.1016/j.tet.2010.03.088
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient stereocontrolled route to (+/-)-cylindricine C is described. Reaction of 9-hydroxynon-1-en-5-one oxime with 2,3-bis(phenylsulfonyl)-1,3-butadiene affords a 7-oxa-1-azanorbornane cycloadduct in high yield. The formation of the bicyclic isoxazolidine arises from conjugate addition of the oxime onto the diene to give a transient nitrone that spontaneously undergoes an intramolecular dipolar cycloaddition. The resulting cycloadduct derived from the cascade sequence was converted into (+/-)-cylindricine C by: (1) a reductive-cyclization to set the BC-ring skeleton, (2) a base-induced cyclization to construct the tricyclic core, and (3) an oxidation-conjugate addition of the n-hexyl side chain to complete the synthesis. (C) 2010 Elsevier Ltd. All rights reserved.
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收藏
页码：3643 / 3650
页数：8
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