Diversity-oriented synthesis of polyketide natural products via iterative chemo- and stereoselective functionalization of polyenoates: Development of a unified approach for the C(1-19) segments of lituarines A-C

被引:27
作者
Smith, AB [1 ]
Walsh, SP
Frohn, M
Duffey, MO
机构
[1] Univ Penn, Monell Chem Senses Ctr, Dept Chem, Philadelphia, PA 19104 USA
[2] Univ Penn, Res Struct Matter Lab, Philadelphia, PA 19104 USA
关键词
D O I
10.1021/ol047792c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A unified, stereocontrolled synthesis of the C(1-19) segments of the lituarines A-C (1-3) has been achieved, highlighted by application of an iterative chemo- and stereoselective trienoate functionalization protocol, a strategy that holds considerable promise for the diversity oriented synthesis of polyketides.
引用
收藏
页码:139 / 142
页数:4
相关论文
共 26 条
[1]   SELECTIVE ASYMMETRIC DIHYDROXYLATION OF POLYENES [J].
BECKER, H ;
SOLER, MA ;
SHARPLESS, KB .
TETRAHEDRON, 1995, 51 (05) :1345-1376
[2]   VICINAL POLYEPOXIDES IN BIOMIMETIC SYNTHESIS - TOTAL SYNTHESIS OF (+/-)-CITREOVIRAL AND RELATED SUBSTITUTED TETRAHYDROFURANS [J].
EBENEZER, W ;
PATTENDEN, G .
TETRAHEDRON LETTERS, 1992, 33 (28) :4053-4056
[3]   EPOXIDES IN SYNTHESIS - STUDIES TOWARDS THE AUROVERTINS [J].
FORBES, JE ;
PATTENDEN, G .
TETRAHEDRON LETTERS, 1987, 28 (24) :2771-2774
[4]   An efficient protocol for the stereoselective dihydroxylation of ene-ester systems [J].
Hermitage, SA ;
Murphy, A ;
Nielsen, P ;
Roberts, SM .
TETRAHEDRON, 1998, 54 (43) :13185-13202
[5]   Enantioselective syntheses of colletodiol, colletol, and grahamimycin A [J].
Hunter, TJ ;
O'Doherty, GA .
ORGANIC LETTERS, 2002, 4 (25) :4447-4450
[6]   CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].
KOLB, HC ;
VANNIEUWENHZE, MS ;
SHARPLESS, KB .
CHEMICAL REVIEWS, 1994, 94 (08) :2483-2547
[7]   A SIMPLIFIED PROCEDURE FOR THE STEREOSPECIFIC TRANSFORMATION OF 1,2-DIOLS INTO EPOXIDES [J].
KOLB, HC ;
SHARPLESS, KB .
TETRAHEDRON, 1992, 48 (48) :10515-10530
[8]   Stereloselective synthesis of the lituarine tricyclic spiroacetal [J].
Robertson, J ;
Meo, P ;
Dallimore, JWP ;
Doyle, BM ;
Hoarau, C .
ORGANIC LETTERS, 2004, 6 (21) :3861-3863
[9]   Syntheses of the C(1-6) and C(19-24) fragments of lituarines A, B, and C [J].
Robertson, J ;
Dallimore, JWP ;
Meo, P .
ORGANIC LETTERS, 2004, 6 (21) :3857-3859
[10]   Organocatalytic asymmetric epoxidation of olefins by chiral ketones [J].
Shi, Y .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :488-496