Synthesis of a simplified sarcodictyin analogue which retains microtubule stabilising properties

被引:31
作者
Telser, J
Beumer, R
Bell, AA
Ceccarelli, SM
Monti, D
Gennari, C
机构
[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
[2] CNR, Ctr Studio Sostanze Organ Nat, I-20133 Milan, Italy
关键词
allylation; antitumour compounds; metathesis; stereocontrol;
D O I
10.1016/S0040-4039(01)02045-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A strategy featuring ring-closing metathesis as key reaction is applied to the synthesis of the sarcodictyin analogue 15. The precursor diene is accessed via a brief and efficient protocol. employing multiple stereoselective allylations. Simplified analogue 15 retains microtubule stabilising properties. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9187 / 9190
页数:4
相关论文
共 55 条
[1]  
Armstrong SK, 1998, J CHEM SOC PERK T 1, P371
[2]   Synthesis of key intermediates for a concise and convergent approach to the marine natural product eleutherobin [J].
Baron, A ;
Caprio, V ;
Mann, J .
TETRAHEDRON LETTERS, 1999, 40 (52) :9321-9324
[3]   Rapid entry into mono-, bi-, and tricyclic β-lactam arrays via alkene metathesis [J].
Barrett, AGM ;
Baugh, SPD ;
Braddock, DC ;
Flack, K ;
Gibson, VC ;
Giles, MR ;
Marshall, EL ;
Procopiou, PA ;
White, AJP ;
Williams, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7893-7907
[4]  
BATTISTINI C, 1996, Patent No. 9636335
[5]  
BOTTA M, UNPUB
[6]  
Bourgeois D, 2000, SYNTHESIS-STUTTGART, P869
[7]   Synthetic transformations of eleutherobin reveal new features of its microtubule-stabilizing pharmacophore [J].
Britton, R ;
de Silva, ED ;
Bigg, CM ;
McHardy, LM ;
Roberge, M ;
Andersen, RJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (35) :8632-8633
[8]   CHIRAL SYNTHESIS VIA ORGANOBORANES .13. A HIGHLY DIASTEREOSELECTIVE AND ENANTIOSELECTIVE ADDITION OF [(Z)-GAMMA-ALKOXYALLYL]DIISOPINOCAMPHEYLBORANES TO ALDEHYDES [J].
BROWN, HC ;
JADHAV, PK ;
BHAT, KS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1535-1538
[9]   HYDROBORATION .61. DIISOPINOCAMPHEYLBORANE OF HIGH OPTICAL PURITY - IMPROVED PREPARATION AND ASYMMETRIC HYDROBORATION OF REPRESENTATIVE CIS-DISUBSTITUTED ALKENES [J].
BROWN, HC ;
DESAI, MC ;
JADHAV, PK .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (26) :5065-5069