The cycloaddition strategy for the synthesis of natural products containing carbocyclic seven-membered rings

被引:230
作者
Battiste, MA
Pelphrey, PM
Wrightthl, DL [1 ]
机构
[1] Dartmouth Coll, Dept Chem, Hanover, NH 03755 USA
[2] Univ Florida, Dept Chem, Gainesville, FL 32611 USA
关键词
cycloaddition; cyclopropene; natural products; oxyallyl cations; seven-membered rings;
D O I
10.1002/chem.200501083
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Highly substituted carbocyclic seven-membered rings are frequently found in natural products and their synthesis represents a significant challenge to the synthetic chemist. Direct intramolecular cyclization of these systems often proves difficult and this fact has catalyzed the development of a variety of strategies based on a convergent intermolecular cycloaddition strategy. This concept article discusses the major cycloaddition approaches utilized to access these types of structures and primarily focuses on examples employed in the synthesis of natural products.
引用
收藏
页码:3438 / 3447
页数:10
相关论文
共 53 条
[21]   A 4+3 cycloaddition approach to the synthesis of (±)-sterpurene [J].
Harmata, M ;
Bohnert, GJ .
ORGANIC LETTERS, 2003, 5 (01) :59-61
[22]   Intramolecular 4+3 cycloadditions. Aspects of stereocontrol in the synthesis of cyclooctanoids. A synthesis of (+)-dactylol [J].
Harmata, M ;
Rashatasakhon, P .
ORGANIC LETTERS, 2000, 2 (18) :2913-2915
[23]   8-oxabicyclo[3.2.1]oct-6-en-3-ones: Application to the asymmetric synthesis of polyoxygenated building blocks [J].
Hartung, IV ;
Hoffmann, HMR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (15) :1934-1949
[24]   A new and efficient strategy for the total synthesis of polycyclic diterpenoids: The preparation of gibberellins (+/-)-GA(103) and (+/-)-GA(73) [J].
King, GR ;
Mander, LN ;
Monck, NJT ;
Morris, JC ;
Zhang, HB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (16) :3828-3829
[25]   Total synthesis of racemic lasidiol via intramolecular [4+3] cycloaddition [J].
Kreiselmeier, G ;
Föhlisch, B .
TETRAHEDRON LETTERS, 2000, 41 (09) :1375-1379
[26]  
Lautens M, 2002, SYNTHESIS-STUTTGART, P1993
[27]   Diastereoselective intermolecular [4+3] cycloadditions via an extended transition state: A route to enantiomerically enriched cycloadducts [J].
Lautens, M ;
Aspiotis, R ;
Colucci, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (44) :10930-10931
[28]   Total synthesis of tropoloisoquinolines: Imerubrine, isoimerubrine, and grandirubrine [J].
Lee, JC ;
Cha, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (14) :3243-3246
[29]   Total synthesis of colchicine.: α-methoxy-substituted oxyallyl [4+3] cycloaddition approach [J].
Lee, JC ;
Jin, SJ ;
Cha, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :2804-2805
[30]   Stereoselective synthesis of the bicyclo[5.3.0]decane portion of the diterpene antibiotic guanacastepene using a pyrylium-ylide [5+2] cycloaddition reaction [J].
Magnus, P ;
Waring, MJ ;
Ollivier, C ;
Lynch, V .
TETRAHEDRON LETTERS, 2001, 42 (30) :4947-4950