Karlotoxin synthetic studies: concise synthesis of a C(42-63) B-ring tetrahydropyran fragment

被引:4
|
作者
Tomioka, Takashi [1 ]
Takahashi, Yusuke [1 ]
Maejima, Toshihide [1 ]
Yabe, Yuki [1 ]
Iwata, Hiroki [1 ]
Hamann, Mark T. [1 ,2 ,3 ,4 ]
机构
[1] Univ Mississippi, Dept Chem & Biochem, University, MS 38677 USA
[2] Univ Mississippi, Dept Pharmacognosy, Sch Pharm, University, MS 38677 USA
[3] Univ Mississippi, Dept Pharmacol, Sch Pharm, University, MS 38677 USA
[4] Univ Mississippi, Natl Ctr Nat Prod Res, Sch Pharm, University, MS 38677 USA
关键词
Polyketide; Karlotoxin; Tetrahydropyran; D-Mannose; Julia-Kocienski olefination; STEREOSELECTIVE-SYNTHESIS; ABSOLUTE-CONFIGURATION; STRUCTURE REVISION; AMPHIDINOL; CENTRAL CORE; LIPID RAFTS; DINOFLAGELLATE; CHOLESTEROL; ACCESS; ROUTE;
D O I
10.1016/j.tetlet.2013.09.104
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Starting from natural D-mannose, a C(42-63) B-ring tetrahydropyran fragment in karlotoxin 2 has been prepared via a common THP intermediate in a concise manner. E-Selective Julia-Kocienski olefination efficiently assembled a C(51-63) chlorodiene subunit and a C(42-50) tetrahydropyran segment. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6584 / 6586
页数:3
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