Macrolactonizations in the total synthesis of natural products

被引:419
作者
Parenty, A
Moreau, X
Campagne, JM
机构
[1] Ecole Normale Super Chim, F-34296 Montpellier, France
[2] Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
D O I
10.1021/cr0301402
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Macrocyclic lactones are lactones with more than 8 atoms in the ring. This paper presents an overview of the macrolactonization of seco-acids in the total synthesis of natural products. Topics discussed are the basics of macrolactonization, macrolactonizations through "acid" activation, and macrolactonizations by "alcohol" activation.
引用
收藏
页码:911 / 939
页数:29
相关论文
共 660 条
[41]   Conformation-directed macrocyclization reactions [J].
Blankenstein, J ;
Zhu, JP .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (10) :1949-1964
[42]   CONVERSION OF AVERMECTIN-B1 TO 19-EPI-AVERMECTIN-B1 [J].
BLIZZARD, T ;
BOSTROM, L ;
MARGIATTO, G ;
MROZIK, H ;
FISHER, M .
TETRAHEDRON LETTERS, 1991, 32 (24) :2723-2726
[43]   Stereoselective syntheses of epothilones A and B via directed nitrile oxide cycloaddition [J].
Bode, JW ;
Carreira, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (15) :3611-3612
[44]   Stereoselective syntheses of epothilones A and B via nitrile oxide cycloadditions and related studies [J].
Bode, JW ;
Carreira, EM .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (19) :6410-6424
[45]  
BODEN CDJ, 1993, SYNTHESIS-STUTTGART, P411, DOI 10.1055/s-1993-25874
[46]   PROTON-TRANSFER STEPS IN STEGLICH ESTERIFICATION - A VERY PRACTICAL NEW METHOD FOR MACROLACTONIZATION [J].
BODEN, EP ;
KECK, GE .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (13) :2394-2395
[47]  
BODO B, 1975, B MUS HIST NAT BELG, V6, P97
[49]  
BOECKMAN RK, 1988, TOTAL SYNTHESIS NATU, V7
[50]   Total synthesis of HUN-7293 [J].
Boger, DL ;
Keim, H ;
Oberhauser, B ;
Schreiner, EP ;
Foster, CA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (26) :6197-6205