Total synthesis of (-)-callystatin A

被引:73
作者
Marshall, JA [1 ]
Bourbeau, MP [1 ]
机构
[1] Univ Virginia, Dept Chem, Charlottesville, VA 22904 USA
关键词
D O I
10.1021/jo016025d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A total synthesis of the cytotoxic polyketide marine natural product callystatin A is described. The route features chiral allenylmetal additions to construct the polypropionate C15-22 segment and an sp(2)-sp(3) Suzuki coupling to join the C1-C11 and C12-C22 subunits.
引用
收藏
页码:2751 / 2754
页数:4
相关论文
共 28 条
[1]   TOTAL SYNTHESIS OF (+/-)-PEDERAMIDE [J].
ADAMS, MA ;
DUGGAN, AJ ;
SMOLANOFF, J ;
MEINWALD, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (18) :5364-5370
[2]   SYNTHETIC STUDIES ON 2R,4',8'R-ALPHA-TOCOPHEROL - APPROACH UTILIZING SIDE-CHAIN SYNTHONS OF MICROBIOLOGICAL ORIGIN [J].
COHEN, N ;
EICHEL, WF ;
LOPRESTI, RJ ;
NEUKOM, C ;
SAUCY, G .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (22) :3505-3511
[3]   TOTAL SYNTHESIS OF LEUKOTRIENE-B5 [J].
COREY, EJ ;
PYNE, SG ;
SU, W .
TETRAHEDRON LETTERS, 1983, 24 (45) :4883-4886
[4]   Asymmetric total synthesis of callystatin A: Asymmetric aldol additions with titanium enolates of acyloxazolidinethiones [J].
Crimmins, MT ;
King, BW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (35) :9084-9085
[5]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156
[6]   TOTAL SYNTHESIS OF (+)-A83543A [(+)-LEPICIDIN-A] [J].
EVANS, DA ;
BLACK, WC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (11) :4497-4513
[7]   NOVEL REAGENT SYSTEM FOR CONVERTING A HYDROXY-GROUP INTO AN IODO-GROUP IN CARBOHYDRATES WITH INVERSION OF CONFIGURATION .3. [J].
GAREGG, PJ ;
JOHANSSON, R ;
ORTEGA, C ;
SAMUELSSON, B .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (03) :681-683
[8]   ELABORATION OF ALDEHYDES AND KETONES TO ALKYNES - IMPROVED METHODOLOGY [J].
GILBERT, JC ;
WEERASOORIYA, U .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (26) :4997-4998
[9]   A 2-STEP, 3-COMPONENT SYNTHESIS OF PGE(1) - UTILIZATION OF ALPHA-IODOENONES IN PD(0)-CATALYZED CROSS-COUPLINGS OF ORGANOBORANES [J].
JOHNSON, CR ;
BRAUN, MP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (23) :11014-11015
[10]   Total synthesis of (-)-callystatin A [J].
Kalesse, M ;
Quitschalle, M ;
Khandavalli, CP ;
Saeed, A .
ORGANIC LETTERS, 2001, 3 (20) :3107-3109