An enantioselective synthesis of the C2-C16 segment of antitumor macrolide laulimalide

被引:44
作者
Ghosh, AK [1 ]
Wang, Y [1 ]
机构
[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA
关键词
D O I
10.1016/S0040-4039(00)00158-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An enantioselective synthesis of the C-2-C-16 Segment of the novel antitumor agent laulimalide is described. The key steps involve a highly diastereoselective allylation, ring-closing olefin metathesis of a homoallylic alcohol derived acrylate ester, a stereoselective anomeric alkylation and an elaboration of an exo-methylene unit by a Julia olefination reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2319 / 2322
页数:4
相关论文
共 21 条
[1]  
*ACS, 1999, 218 AM CHEM SOC NAT
[2]   LAULIMALIDES - NEW POTENT CYTO-TOXIC MACROLIDES FROM A MARINE SPONGE AND A NUDIBRANCH PREDATOR [J].
CORLEY, DG ;
HERB, R ;
MOORE, RE ;
SCHEUER, PJ ;
PAUL, VJ .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) :3644-3646
[3]   General synthesis of alpha-acetoxy ethers from esters by DIBALH reduction and acetylation [J].
Dahanukar, VH ;
Rychnovsky, SD .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :8317-8320
[4]   ON THE ADDITION OF ALLYLTRIMETHYLSILANE TO GLYCAL ACETATES [J].
DANISHEFSKY, S ;
KERWIN, JF .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (19) :3803-3805
[5]   Ring-closing metathesis strategy to unsaturated γ- and δ-lactones:: Synthesis of hydroxyethylene isostere for protease inhibitors [J].
Ghosh, AK ;
Cappiello, J ;
Shin, D .
TETRAHEDRON LETTERS, 1998, 39 (26) :4651-4654
[6]   Synthetic studies of antitumor macrolide laulimalide: Enantioselective synthesis of the C-3-C-14 segment by a catalytic hetero Diels-Alder strategy [J].
Ghosh, AK ;
Packiarajan, M ;
Cappiello, J .
TETRAHEDRON LETTERS, 1997, 38 (14) :2427-2430
[7]  
Harris CR, 1999, J ORG CHEM, V64, P8434
[8]   CHIRAL SYNTHESIS VIA ORGANOBORANES .5. ASYMMETRIC ALLYLBORATION VIA CHIRAL ALLYLDIALKYLBORANES - SYNTHESIS OF HOMOALLYLIC ALCOHOLS WITH EXCEPTIONALLY HIGH ENANTIOMERIC EXCESS [J].
JADHAV, PK ;
BHAT, KS ;
PERUMAL, PT ;
BROWN, HC .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :432-439
[9]   Structures and absolute configurations of the marine toxins, latrunculin A and laulimalide [J].
Jefford, CW ;
Bernardinelli, G ;
Tanaka, J ;
Higa, T .
TETRAHEDRON LETTERS, 1996, 37 (02) :159-162
[10]   TOTAL SYNTHESIS OF (+)-CARBONOLIDE-B [J].
KECK, GE ;
PALANI, A ;
MCHARDY, SF .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :3113-3122