Efficient asymmetric synthesis of (+)-SCH 351448

被引:30
作者
Bolshakov, S [1 ]
Leighton, JL [1 ]
机构
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
关键词
D O I
10.1021/ol0515006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and stereocontrolled total synthesis of (+)-SCH 351448, a novel activator of low-density lipoprotein receptor promoter, has been achieved with a longest linear sequence of 21 steps. Key steps include applications of the recently developed asymmetric allyl- and crotylsilane reagents and a new protodesilylative version of the tandem silylformylation/allyisilylation reaction, which provides an efficient synthesis of 1,5-syn-diols.
引用
收藏
页码:3809 / 3812
页数:4
相关论文
共 19 条
[1]   Synthesis of the C1-C21 (C1′-C21′) fragment of the dimeric polyketide natural product SCH 351448 [J].
Bhattacharjee, A ;
Soltani, O ;
De Brabander, JK .
ORGANIC LETTERS, 2002, 4 (04) :481-484
[3]   A RECEPTOR-MEDIATED PATHWAY FOR CHOLESTEROL HOMEOSTASIS [J].
BROWN, MS ;
GOLDSTEIN, JL .
SCIENCE, 1986, 232 (4746) :34-47
[4]   A general model for selectivity in olefin cross metathesis [J].
Chatterjee, AK ;
Choi, TL ;
Sanders, DP ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) :11360-11370
[5]  
DESS DB, 1983, J ORG CHEM, V48, P4156
[6]   Efficient enantioselective synthesis of functionalized tetrahydropyrans by Ru-catalyzed asymmetric ring-opening metathesis/cross-metathesis (AROM/CM) [J].
Gillingham, DG ;
Kataoka, O ;
Garber, SB ;
Hoveyda, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (39) :12288-12290
[7]   Highly diastereo- and enantioselective reagents for aldehyde crotylation [J].
Hackman, BM ;
Lombardi, PJ ;
Leighton, JL .
ORGANIC LETTERS, 2004, 6 (23) :4375-4377
[8]   SILOXANES - VERSATILE TEMPLATES FOR ACYCLIC STEREOCONTROL - SYNTHESIS OF THE C27-C33 SEGMENT OF RAPAMYCIN [J].
HALE, MR ;
HOVEYDA, AH .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1643-1645
[9]   A novel microbial metabolite, activator of low density lipoprotein receptor promoter [J].
Hegde, VR ;
Puar, MS ;
Dai, P ;
Patel, M ;
Gullo, VP ;
Das, PR ;
Bond, RW ;
McPhail, AT .
TETRAHEDRON LETTERS, 2000, 41 (09) :1351-1354
[10]   Total synthesis of (+)-SCH 351448 [J].
Kang, EJ ;
Cho, EJ ;
Lee, YE ;
Ji, MK ;
Shin, DM ;
Chung, YK ;
Lee, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (09) :2680-2681