A formal synthesis of (+)-didemniserinolipid B employing a Pd-mediated 6-endo selective alkynediol cycloisomerization

被引:24
作者
Ramana, C. V. [1 ]
Induvadana, Boddeti [1 ]
机构
[1] Natl Chem Lab, Pune 411008, Maharashtra, India
关键词
Didemniserinolipid; Bridged bicyclic ketal; Alkynol cycloisomerization; Zipper reaction; Yamaguchi oxirane alkyne coupling; NATURAL-PRODUCT; CATALYZED CYCLOISOMERIZATION; EFFICIENT METHOD; SUGAR ALKYNOLS; PALLADIUM; TRANSFORMATION; ACETALS; HYDROALKOXYLATION; CONFIGURATION; HETEROCYCLES;
D O I
10.1016/j.tetlet.2008.10.137
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we describe a concise assembly of central 6,8-dioxabicyclo[3,2,1]octane core of didemniserino-lipid by employing a Pd-mediated alkynediol cycloisomerization and a formal total synthesis of didemniserinolipid (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:271 / 273
页数:3
相关论文
共 43 条
[1]  
Abrams SR, 1993, ORG SYNTH, V8, P146
[2]   Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].
Alonso, F ;
Beletskaya, IP ;
Yus, M .
CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159
[3]   Highly efficient access to strained bicyclic ketals via gold-catalyzed cycloisomerization of bis-homopropargylic diols [J].
Antoniotti, S ;
Genin, E ;
Michelet, V ;
Genêt, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (28) :9976-9977
[4]  
Arndt S, 2001, CHEM-EUR J, V7, P993, DOI 10.1002/1521-3765(20010302)7:5<993::AID-CHEM993>3.0.CO
[5]  
2-S
[6]   Marine natural products [J].
Blunt, John W. ;
Copp, Brent R. ;
Hu, Wan-Ping ;
Munro, Murray H. G. ;
Northcote, Peter T. ;
Prinsep, Michele R. .
NATURAL PRODUCT REPORTS, 2008, 25 (01) :35-94
[7]   Marine natural products [J].
Blunt, JW ;
Copp, BR ;
Munro, MHG ;
Northcote, PT ;
Prinsep, MR .
NATURAL PRODUCT REPORTS, 2003, 20 (01) :1-48
[8]   SALINE HYDRIDES AND SUPERBASES IN ORGANIC REACTIONS .9. ACETYLENE ZIPPER - EXCEPTIONALLY FACILE CONTRATHERMODYNAMIC MULTIPOSITIONAL ISOMERIZATION OF ALKYNES WITH POTASSIUM 3-AMINOPROPYLAMIDE [J].
BROWN, CA ;
YAMASHITA, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (04) :891-892
[9]   PtCl4-catalyzed domino synthesis of fused bicyclic acetals [J].
Dieguez-Vazquez, Alejandro ;
Tzschucke, C. Christoph ;
Lam, Wing Yee ;
Ley, Steven V. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (01) :209-212
[10]  
Dondoni A., 2004, ORG SYNTH, V10, P320