Investigations into a biomimetic approach toward CP-225,917 and CP-263,114

被引:56
作者
Sulikowski, GA [1 ]
Agnelli, F [1 ]
Corbett, RM [1 ]
机构
[1] Texas A&M Univ, Dept Chem, College Stn, TX 77842 USA
关键词
D O I
10.1021/jo9911286
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A biosynthesis of the structurally complex nonadride CP-225,917 (1) is outlined. A key step in this proposal is the dimerization of a C-16 anhydride derived from the condensation of lauric acid and oxaloacetic acid. An important element of this step is a templating effect imposed by two thioester linkages, reminiscent of a polyketide or fatty acid synthase pathway. On the basis of this principle, the dimerization of two C-11 anhydrides, templated by a 1,n-diol tether, leading to the core structure of CP-225,917 and CP-263,114 was investigated.
引用
收藏
页码:337 / 342
页数:6
相关论文
共 36 条
[1]   Synthesis of arylacetates by the palladium-catalyzed cross-coupling of aryl bromides and copper(II) enolates [J].
Agnelli, F ;
Sulikowski, GA .
TETRAHEDRON LETTERS, 1998, 39 (48) :8807-8810
[2]  
Armstrong A, 1998, SYNLETT, P552
[3]  
BALDWIN J E, 1962, Experientia, V18, P345, DOI 10.1007/BF02172243
[4]   Reinvestigation of the dimerisation process forming isoglaucanic acid [J].
Baldwin, JE ;
Beyeler, A ;
Cox, RJ ;
Keats, C ;
Pritchard, GJ ;
Adlington, RM ;
Watkin, DJ .
TETRAHEDRON, 1999, 55 (23) :7363-7374
[5]  
BARTON DH, 1996, J CHEM SOC, P1779
[6]   NONADRIDES .2. CONSTITUTIONS OF GLAUCONIC AND GLAUCANIC ACIDS [J].
BARTON, DHR ;
JACKMAN, LM ;
RODRIGUE.L ;
SUTHERLAND, JK .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (MAR) :1772-+
[7]   NONADRIDES .I. INTRODUCTION AND GENERAL SURVEY [J].
BARTON, DHR ;
SUTHERLA.JK .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (MAR) :1769-&
[8]   An approach to the synthesis of CP-263,114: A remarkably facile silyloxy-cope rearrangement [J].
Bio, MM ;
Leighton, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (04) :890-891
[9]   NONADRIDES .V. BISOYNTHESIS OF GLAUCONIC ACID [J].
BLOOMER, JL ;
MOPPETT, CE ;
SUTHERLAND, JK .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (05) :588-+
[10]   Stereospecific synthesis of the CP-263,114 core structure [J].
Chen, C ;
Layton, ME ;
Shair, MD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (41) :10784-10785