Studies on the total synthesis of macrolactin A.: A stereoselective synthesis of the C3-C13 and C14-C24 fragments

被引:23
作者
Li, SK [1 ]
Xu, R [1 ]
Bai, DL [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 200031, Peoples R China
基金
中国国家自然科学基金;
关键词
macrolactin A; antiviral; stereoselective synthesis; Wittig olefination; sulfone alkylation;
D O I
10.1016/S0040-4039(00)00412-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthetic studies towards the C-3-C-13 (2) and C-14-C-24 (3) segments of the potent antiviral and antitumor compound macrolactin A (1) are presented. Segment 2 was constructed via a convergent and facile approach, exploiting Wittig olefination to generate the sensitive E,Z-diene moiety. Segment 3 was obtained from the chiral pool derived sulfone 4 via an alpha-alkylation-desulfonation reaction sequence. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3463 / 3466
页数:4
相关论文
共 21 条
[1]   AN APPROACH TO PSEUDOMONIC ACIDS FROM ACETYLENIC PRECURSORS - SYNTHESIS OF 2-(HYDROXYMETHYL)-3-BUTYN-1-OL [J].
BATES, HA ;
FARINA, J ;
TONG, M .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (14) :2637-2641
[2]  
BENVEGNU T, 1994, SYNLETT, P505
[3]   Stereoselective synthesis of macrolactin A analogues .1. The C-7-C-20 fragment [J].
Benvegnu, TJ ;
Toupet, LJ ;
Gree, RL .
TETRAHEDRON, 1996, 52 (36) :11811-11820
[4]   Sequential sp(2)-sp(2) coupling reactions in polyene macrolide synthesis. A novel approach to macrolactin A [J].
Boyce, RJ ;
Pattenden, G .
TETRAHEDRON LETTERS, 1996, 37 (20) :3501-3504
[5]  
CRISTAU HJ, 1979, SYNTHESIS-STUTTGART, P538
[6]   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
[7]   MODEL STUDIES TOWARD THE SYNTHESIS OF MACROLACTIN-A - ORGANOIRON METHODOLOGY FOR INTRODUCTION OF THE C1-C-11 AND C16-C24 SEGMENTS [J].
DONALDSON, WA ;
BELL, PT ;
WANG, Z ;
BENNETT, DW .
TETRAHEDRON LETTERS, 1994, 35 (32) :5829-5832
[8]   Asymmetric acetate aldol reactions in connection with an enantioselective total synthesis of macrolactin A [J].
Gonzalez, A ;
Aiguade, J ;
Urpi, F ;
Vilarrasa, J .
TETRAHEDRON LETTERS, 1996, 37 (49) :8949-8952
[9]   THE MACROLACTINS, A NOVEL CLASS OF ANTIVIRAL AND CYTO-TOXIC MACROLIDES FROM A DEEP-SEA MARINE BACTERIUM [J].
GUSTAFSON, K ;
ROMAN, M ;
FENICAL, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (19) :7519-7524
[10]   STEREOCONTROLLED SYNTHESIS OF THE SPIRO KETAL UNIT OF AVERMECTIN-B1A AGLYCON [J].
HANESSIAN, S ;
UGOLINI, A ;
THERIEN, M .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (23) :4427-4430