Total synthesis of (-)-callystatin A

被引:61
作者
Langille, NF
Panek, JS
机构
[1] Boston Univ, Dept Chem, Boston, MA 02215 USA
[2] Boston Univ, Ctr Chem Methodol & Library Dev, Metcalf Ctr Sci & Engn, Boston, MA 02215 USA
关键词
D O I
10.1021/ol048664r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convergent enantioselective synthesis of the natural product (-)-callystatin A (1) is described. Key features of the synthesis include a lipase-mediated kinetic resolution to install the C5 lactone stereochemistry, a hydrozirconation-based approach to the C8-C9 trisubstituted (Z)-olefin, and a stereoselective cross-coupling of a vinyl dibromide to install the C14-C15 trisubstituted (E)-olefin.
引用
收藏
页码:3203 / 3206
页数:4
相关论文
共 35 条
[1]   Stereoselective synthesis of functionalized trisubstituted olefins via palladium(0)-catalyzed cross-coupling reaction [J].
Arefolov, A ;
Langille, NF ;
Panek, JS .
ORGANIC LETTERS, 2001, 3 (21) :3281-3284
[2]   Enzyme-mediated regioselective acylations of sophorolipids [J].
Bisht, KS ;
Gross, RA ;
Kaplan, DL .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :780-789
[3]  
Chavez DE, 2001, ANGEW CHEM INT EDIT, V40, P3667, DOI 10.1002/1521-3773(20011001)40:19<3667::AID-ANIE3667>3.0.CO
[4]  
2-6
[5]  
COREY EJ, 1972, TETRAHEDRON LETT, P3769
[6]   Asymmetric total synthesis of callystatin A: Asymmetric aldol additions with titanium enolates of acyloxazolidinethiones [J].
Crimmins, MT ;
King, BW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (35) :9084-9085
[7]   Synthesis of C1-C11 fragment of callystatin A [J].
Dias, LC ;
Meira, PRR .
TETRAHEDRON LETTERS, 2002, 43 (49) :8883-8885
[8]   Synthesis of C13-C22 fragment of the marine sponge polyketide callystatin A (vol 43, pg 185, 2002) [J].
Dias, LC ;
Meira, PRR .
TETRAHEDRON LETTERS, 2002, 43 (08) :1593-1593
[9]   Synthesis of C13-C22 fragment of the marine sponged polyketide callystatin A [J].
Dias, LC ;
Meira, PRR .
TETRAHEDRON LETTERS, 2002, 43 (02) :185-187
[10]   RING-CLOSING METATHESIS AND RELATED PROCESSES IN ORGANIC-SYNTHESIS [J].
GRUBBS, RH ;
MILLER, SJ ;
FU, GC .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (11) :446-452