A short approach to chaetomellic anhydride A from 2,2-dichloropalmitic acid: elucidation of the mechanism governing the functional rearrangement of the chlorinated pyrrolidin-2-one intermediate

被引：41
作者：
Bellesia, F
Danieli, C
De Buyck, L
Galeazzi, R
Ghelfi, F
Mucci, A
Orena, M
Pagnoni, UM
Parsons, AF
Roncaglia, F
机构：
[1] Univ Modena, Dipartimento Chim, I-41100 Modena, Italy
[2] Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium
[3] Univ Ancona, Dipartimento Sci Mat & Terra, I-60131 Ancona, Italy
[4] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
来源：
TETRAHEDRON | 2006年 / 62卷 / 04期
关键词：
halocompound; pyrrolidinone; radical reaction; rearrangement;
D O I：
10.1016/j.tet.2005.09.140
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Chaetomellic anhydride A was efficiently attained in three steps, starting from 2,2-dichloropalmitic acid and 2-(3-chloro-2-propenylamino)pyridine. Atom transfer radical cyclisation selectively formed the cis-stereoisomer of the trichloropyrrolidin-2-one, which underwent a stereospecific functional rearrangement to form a substituted maleimide. The choice of 2-pyridyl, as 'cyclisation auxiliary' in the atom transfer radical cyclisation step, proved beneficial for hydrolysis of the maleimide to form the desired anhydride. (c) 2005 Elsevier Ltd. All rights reserved.
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收藏
页码：746 / 757
页数：12
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