Synthesis of two diastereomeric C1-C22 fragments of spirastrellolide A

被引:44
作者
Paterson, Ian [1 ]
Anderson, Edward A. [1 ]
Dalby, Stephen M. [1 ]
Genovino, Julien [1 ]
Lim, Jong Ho [1 ]
Moessner, Christian [1 ]
机构
[1] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England
关键词
D O I
10.1039/b700827a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The optimisation of a synthetic strategy towards the ABC segment of the cytotoxic macrolide spirastrellolide A is reported, together with its application to the synthesis of two diastereomeric C-1 - C-22 fragments for stereochemical correlation purposes with a putative spirastrellolide degradation product.
引用
收藏
页码:1852 / 1854
页数:3
相关论文
共 27 条
[1]   Synthesis of functionalized olefins by cross and ring-closing metatheses [J].
Chatterjee, AK ;
Morgan, JP ;
Scholl, M ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (15) :3783-3784
[2]  
Corey E.J., 1972, TETRAHEDRON, V36, P3769
[3]   DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE [J].
EVANS, DA ;
CHAPMAN, KT ;
CARREIRA, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3560-3578
[4]   Toward the total synthesis of spirastrellolide A.: Part 1:: Strategic considerations and preparation of the southern domain [J].
Fuerstner, Alois ;
Fenster, Michael D. B. ;
Fasching, Bernhard ;
Godbout, Cedrickx ;
Radkowski, Karin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (33) :5506-5510
[5]   Toward the total synthesis of spirastrellolide A.: Part 2:: Conquest of the northern hemisphere [J].
Fuerstner, Alois ;
Fenster, Michael D. B. ;
Fasching, Bernhard ;
Godbout, Cedrickx ;
Radkowski, Karin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (33) :5510-5515
[6]   Regulators of serine/threonine protein phosphatases at the dawn of a clinical era? [J].
Honkanen, RE ;
Golden, T .
CURRENT MEDICINAL CHEMISTRY, 2002, 9 (22) :2055-2075
[7]   Phase I and pharmacokinetic study of fostriecin given as an intravenous bolus daily for five consecutive days [J].
Lê, LH ;
Erlichman, C ;
Pillon, L ;
Thiessen, JJ ;
Day, A ;
Wainman, N ;
Eisenhauer, EA ;
Moore, MJ .
INVESTIGATIONAL NEW DRUGS, 2004, 22 (02) :159-167
[8]   Synthesis of the C11-C23 fragment of spirastrellolide A. A ketal-tethered RCM approach to the construction of spiroketals [J].
Liu, J ;
Hsung, RP .
ORGANIC LETTERS, 2005, 7 (11) :2273-2276
[9]   Synthesis of the C1-C16 fragment of spirastrellolide A [J].
Liu, Jia ;
Yang, Jin Haek ;
Ko, Changhong ;
Hsung, Richard P. .
TETRAHEDRON LETTERS, 2006, 47 (34) :6121-6123
[10]   TOTAL SYNTHESIS OF BIOACTIVE MARINE MACROLIDES [J].
NORCROSS, RD ;
PATERSON, I .
CHEMICAL REVIEWS, 1995, 95 (06) :2041-2114