Development of a concise and diversity-oriented approach for the synthesis of plecomacrolides via the diene-ene RCM

被引:40
作者
Lu, K [1 ]
Huang, MW [1 ]
Xiang, Z [1 ]
Liu, YX [1 ]
Chen, JH [1 ]
Yang, Z [1 ]
机构
[1] Peking Univ, Key Lab Bioorgan Chem & Mol Engn,Lab Chem Genet, Minist Educ,Sch Pharmaceut Sci,Shenzhen Grad Sch, Coll Chem,State Key Lab Nat & Biomimet Drugs, Beijing 100871, Peoples R China
关键词
D O I
10.1021/ol060221v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise synthesis of the core structures of plecomacrolide with ring sizes varying from 16 to 19 atoms was achieved for the first time by the diene-ene ring-closing olefin metathesis reaction. This approach should allow access to the structurally diverse analogues of plecomacrolide.
引用
收藏
页码:1193 / 1196
页数:4
相关论文
共 58 条
[1]   A CONFORMATIONAL STUDY OF BAFILOMYCIN-A1 BY X-RAY CRYSTALLOGRAPHY AND NMR TECHNIQUES [J].
BAKER, GH ;
BROWN, PJ ;
DORGAN, RJJ ;
EVERETT, JR ;
LEY, SV ;
SLAWIN, AMZ ;
WILLIAMS, DJ .
TETRAHEDRON LETTERS, 1987, 28 (45) :5565-5568
[2]   Highly concise routes to epothilones: The total synthesis and evaluation of epothilone 490 [J].
Biswas, K ;
Lin, H ;
Njardarson, JT ;
Chappell, MD ;
Chou, TC ;
Guan, YB ;
Tong, WP ;
He, LF ;
Horwitz, SB ;
Danishefsky, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (33) :9825-9832
[3]   BAFILOMYCINS - A CLASS OF INHIBITORS OF MEMBRANE ATPASES FROM MICROORGANISMS, ANIMAL-CELLS, AND PLANT-CELLS [J].
BOWMAN, EJ ;
SIEBERS, A ;
ALTENDORF, K .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1988, 85 (21) :7972-7976
[4]  
Cabrejas LMM, 1999, ANGEW CHEM INT EDIT, V38, P2443
[5]  
Clark JS, 1997, TETRAHEDRON LETT, V38, P127
[6]   Synthesis of muscothiazoles A and B: Critical role of methyl group substitution in RCM-based syntheses of macrocycles [J].
Commeureuc, AGJ ;
Murphy, JA ;
Dewis, ML .
ORGANIC LETTERS, 2003, 5 (16) :2785-2788
[7]   Recent developments in olefin cross-metathesis [J].
Connon, SJ ;
Blechert, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (17) :1900-1923
[8]   Asymmetric aldol-ring-closing metathesis strategy for the enantioselective construction of six- to nine-membered oxygen heterocycles [J].
Crimmins, MT ;
Choy, AL .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7548-7549
[9]   Structures and total syntheses of the plecomacrolides [J].
Dai, WM ;
Guan, YC ;
Jin, J .
CURRENT MEDICINAL CHEMISTRY, 2005, 12 (17) :1947-1993
[10]   CHEMICAL MODIFICATIONS OF BAFILOMYCIN-TYPE 16-MEMBERED DIENLACTONE MACROLIDES [J].
DEEG, M ;
HAGENMAIER, H ;
KRETSCHMER, A .
JOURNAL OF ANTIBIOTICS, 1987, 40 (03) :320-328