Total Synthesis of the Anti-Apoptotic Agents Iso- and Bongkrekic Acids

被引:78
作者
Francais, Antoine [1 ]
Leyva, Antonio [1 ]
Etxebarria-Jardi, Gorka [1 ]
Ley, Steven V. [1 ]
机构
[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
基金
英国工程与自然科学研究理事会;
关键词
CROSS-COUPLING REACTIONS; ISOBONGKREKIC ACID; NATURAL-PRODUCT; STRATEGY; TRANSLOCATION; MITOCHONDRIA; CYCLIZATION; INHIBITOR; OXIDATION; ALCOHOLS;
D O I
10.1021/ol902676t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first convergent total synthesis of isobongkrekic acid is reported Involving three different stereospecific palladium cross-couplings for the formation of the diene units. Access to bongkrekic acid by this route Is also demonstrated. These syntheses involve the formation of several potentially general building blocks.
引用
收藏
页码:340 / 343
页数:4
相关论文
共 50 条
[1]  
ARNAP J, 1975, J CARBOHYDR RES, V44, pC5
[2]   IMPROVED STEREOSELECTIVE REDUCTION OF A E,E, CONJUGATED DIENYNE TO A E,E,Z CONJUGATED TRIENE [J].
AVIGNONTROPIS, M ;
POUGNY, JR .
TETRAHEDRON LETTERS, 1989, 30 (37) :4951-4952
[3]   TOTAL SYNTHESIS OF (+)-MACBECIN-I [J].
BAKER, R ;
CASTRO, JL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (01) :47-65
[4]   The kinetic resolution of allylic alcohols by a non-enzymatic acylation catalyst; application to natural product synthesis [J].
Bellemin-Laponnaz, S ;
Tweddell, J ;
Ruble, JC ;
Breitling, FM ;
Fu, GC .
CHEMICAL COMMUNICATIONS, 2000, (12) :1009-1010
[5]  
BOLLAND W, 1987, HELV CHIM ACTA, V70, P1025
[6]   ON THE STRUCTURE OF ISOBONGKREKIC ACID, A NOVEL DELTA-2-E ISOMER OF THE ANTIBIOTIC BONGKREKIC ACID [J].
CHATTERJEE, S ;
VIJAYAKUMAR, EKS ;
ROY, K ;
RUPP, RH ;
GANGULI, BN .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (20) :4883-4886
[7]   Zinc-acetic acid reductive cyclisation in a two-step synthesis of the S1-N10 nine-membered lactone core of ent-griseoviridin [J].
Chaume, G ;
Kuligowski, C ;
Bezzenine-Laffolée, S ;
Ricard, L ;
Pancrazi, A ;
Ardisson, J .
SYNTHESIS-STUTTGART, 2004, (18) :3029-3036
[8]   APPLICATION OF THE IBUKA-YAMAMOTO REACTION TO A PROBLEM IN STEREOCHEMICAL COMMUNICATION - A STRATEGY FOR THE STEREOSPECIFIC SYNTHESIS AND STABILIZATION OF THE TRIENE SUBSTRUCTURE OF RAPAMYCIN THROUGH SULFONE SUBSTITUTION [J].
CHEN, SH ;
HORVATH, RF ;
JOGLAR, J ;
FISHER, MJ ;
DANISHEFSKY, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5834-5845
[9]   TOTAL SYNTHESIS OF BONGKREKIC ACID [J].
COREY, EJ ;
TRAMONTANO, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (02) :462-463
[10]  
de Bruijn J., 1973, Tetrahedron, V29, P1541