Stereoselective synthesis of the bicyclo[5.3.0]decane portion of the diterpene antibiotic guanacastepene using a pyrylium-ylide [5+2] cycloaddition reaction

被引：52

作者：

Magnus, P ^{[1
]}

Waring, MJ ^{[1
]}

Ollivier, C ^{[1
]}

Lynch, V ^{[1
]}

机构：

[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 30期

关键词：

guanacastepene; antibiotic; pyrylium-ylide; conjugate addition;

D O I：

10.1016/S0040-4039(01)00851-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of 14 with Ac2O/Et3N resulted in [5+2] cyclization to give 2, which was further elaborated into 20, thus establishing the required stereochemistry in the top-half of guanacastepene 1. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：4947 / 4950

页数：4

共 7 条

[1] Stereoselective synthesis of the bicyclo[5.3.0]decane portion of the diterpene antibiotic guanacastepene using a pyrylium-ylide [5+2] cycloaddition reaction (vol 42, pg 4947, 2001)
Magnus, P
Waring, MJ
Ollivier, C
Lynch, V
TETRAHEDRON LETTERS, 2001, 42 (39) : 6977 - 6977
[2] Stereoselective synthesis of cycloheptanone derivatives via an intermolecular [5+2] cycloaddition reaction
Tanino, K
Kondo, F
Shimizu, T
Miyashita, M
ORGANIC LETTERS, 2002, 4 (13) : 2217 - 2219
[3] Synthesis of 1-acetyl-2-silyoxycycloheptane derivatives via highly stereoselective formal [5+2] cycloaddition reaction
Kudo, Mami
Kondo, Fumikatsu
Maekawa, Hideki
Shimizu, Tadashi
Miyashita, Masaaki
Tanino, Keiji
TETRAHEDRON LETTERS, 2014, 55 (06) : 1192 - 1195
[4] Transfer of Chirality in the Rhodium-Catalyzed Intramolecular [5+2] Cycloaddition of 3-Acyloxy-1,4-enynes (ACEs) and Alkynes: Synthesis of Enantioenriched Bicyclo[5.3.0]decatrienes
Shu, Xing-zhong
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Song, Wangze
Guzei, Ilia A.
Tang, Weiping
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (51) : 13601 - 13605
[5] Highly stereoselective 7-membered ring synthesis based upon the oxidopyrylium-alkene [5+2]cycloaddition reaction
Ohmori, N
Miyazaki, T
Kojima, S
Ohkata, K
CHEMISTRY LETTERS, 2001, (09) : 906 - 907
[6] Formal total synthesis of (±)-hirsutic acid C using the tandem Rh(I)-catalyzed [(5+2)+1] cycloaddition/aldol reaction
Yuan, Changxia
Jiao, Lei
Yu, Zhi-Xiang
TETRAHEDRON LETTERS, 2010, 51 (43) : 5674 - 5676
[7] An Atom-Economic Synthesis of Bicyclo[3.1.0]hexanes by Rhodium N-Heterocyclic Carbene-Catalyzed Diastereoselective Tandem Hetero-[5+2] Cycloaddition/Claisen Rearrangement Reaction of Vinylic Oxiranes with Alkynes
Feng, Jian-Jun
Zhang, Junliang
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (19) : 7304 - 7307

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