Synthesis of the C5-C30 fragment of cyclodidemniserinol trisulfate via I2-mediated deprotection and ring closure tandem reaction

被引：7
|
作者：
Liu, Jian-Hua [1 ]
Jin, Yi [1 ]
Long, Ya-Qiu [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Biol Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
来源：
TETRAHEDRON | 2010年 / 66卷 / 06期
基金：
中国国家自然科学基金;
关键词：
CORE STRUCTURE CONSTRUCTION; TUNICATE DIDEMNUM SP; ABSOLUTE-CONFIGURATION; NATURAL-PRODUCT; STEREOCHEMISTRY; INTEGRASE; ESTERS; HIV-1; ACID;
D O I：
10.1016/j.tet.2009.12.024
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Marine natural product cyclodidemniserinol trisulfate displayed moderate HIV-I integrase Inhibitory activity Irs novel structure triggered Out interest to synthesize it In our total synthesis effort, the natural product was dissected into four fragments based oil the rational retrosynthetic analysis All four fragments were successfully prepared with orthogonal protection And lie assembly of fragment A and B furnished the C-5-C-30 key subunit by employing the I-2-mediated deprotection intramolecular ketal formation tandem reaction in the presence of NaHO3 in MeCN Our work provided flexible and practical approaches to synthesize and derive the 3,5,7-trisubstituted 6,8-dioxabicyclo [3 2 1] octane based analogs to search for new structure HIV-I integrase inhibitors (C) 2009 Elsevier Lid All rights reserved
引用
收藏
页码：1267 / 1273
页数：7
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