A preliminary evaluation of a metathesis approach to bryostatins

被引:42
作者
Ball, M [1 ]
Bradshaw, BJ [1 ]
Dumeunier, R [1 ]
Gregson, TJ [1 ]
MacCormick, S [1 ]
Omori, H [1 ]
Thomas, EJ [1 ]
机构
[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/j.tetlet.2006.01.097
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Preliminary investigations into the synthesis of bryostatins using ring-closing metathesis to form the C(16)-C(17) double bond led to a synthesis of the bryostatin analogue 51; precursors 26 and 52, which possess the geminal dimethyl group at G 18, did not undergo the required ring-closing metathesis. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2223 / 2227
页数:5
相关论文
共 18 条
[1]   Synthesis of the C(17)-C(27) fragment of the 20-deoxybryostatins [J].
Almendros, P ;
Rae, A ;
Thomas, EJ .
TETRAHEDRON LETTERS, 2000, 41 (49) :9565-9568
[2]   A stereoselective synthesis of the C(1)-C(16) fragment of the bryostatins [J].
Ball, M ;
Baron, A ;
Bradshaw, B ;
Omori, H ;
MacCormick, S ;
Thomas, EJ .
TETRAHEDRON LETTERS, 2004, 45 (47) :8737-8740
[3]   Total synthesis of bryostatin 2 [J].
Evans, DA ;
Carter, PH ;
Carreira, EM ;
Charette, AB ;
Prunet, JA ;
Lautens, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (33) :7540-7552
[4]  
Evans DA, 1998, ANGEW CHEM INT EDIT, V37, P2354, DOI 10.1002/(SICI)1521-3773(19980918)37:17<2354::AID-ANIE2354>3.0.CO
[5]  
2-9
[6]  
FRICK JA, 1992, SYNTHESIS-STUTTGART, P621
[7]  
GRACIA J, 1998, J CHEM SOC P1, P2853
[8]   The chemistry and biology of the bryostatin antitumour macrolides [J].
Hale, KJ ;
Hummersone, MG ;
Manaviazar, S ;
Frigerio, M .
NATURAL PRODUCT REPORTS, 2002, 19 (04) :413-453
[9]   SYNTHESIS OF BRYOSTATIN-7 [J].
KAGEYAMA, M ;
TAMURA, T ;
NANTZ, MH ;
ROBERTS, JC ;
SOMFAI, P ;
WHRITENOUR, DC ;
MASAMUNE, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (20) :7407-7408
[10]   An efficient approach to Aspidosperma alkaloids via [4+2] cycloadditions of aminosiloxydienes:: Stereocontrolled total synthesis of (±)-tabersonine.: Gram-scale catalytic asymmetric syntheses of (+)-tabersonine and (+)-16-methoxytabersonine.: Asymmetric syntheses of (+)-aspidospermidine and (-)-quebrachamine [J].
Kozmin, SA ;
Iwama, T ;
Huang, Y ;
Rawal, VH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (17) :4628-4641