Studies towards the biomimetic synthesis of the nonadrides CP-225,917 and CP-263,114

被引:22
作者
Baldwin, JE [1 ]
Adlington, RM [1 ]
Roussi, F [1 ]
Bulger, PG [1 ]
Marquez, R [1 ]
Mayweg, AVW [1 ]
机构
[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England
关键词
nonadrides; biomimetic synthesis; intramolecular cyclisation; bis-anhydride dimers;
D O I
10.1016/S0040-4020(01)00706-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Intramolecular cyclisations of dimeric bis-anhydride compounds have been investigated, to help elucidate the biosynthesis of the nonadride family of compounds. Short and efficient syntheses of these bis-anhydride compounds, together with their cyclisations to yield analogues of glaucanic and iso-glaucanic acid, are described herein. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7409 / 7416
页数:8
相关论文
共 53 条
[1]  
Armstrong A, 1998, SYNLETT, P552
[2]   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
[3]   Stereoconvergent palladium-catalyzed carbonylation of both E and Z isomers of a 2-trifloxy-1,3-butadiene [J].
Bio, MM ;
Leighton, JL .
ORGANIC LETTERS, 2000, 2 (18) :2905-2907
[4]   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
[5]   Synthesis of (+)-CP-263,114 [J].
Chen, C ;
Layton, ME ;
Sheehan, SM ;
Shair, MD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (30) :7424-7425
[6]   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
[7]   Model studies related to CP-225,917: Stereocontrolled generation of the quaternary center [J].
Clive, DLJ ;
Zhang, JH .
TETRAHEDRON, 1999, 55 (41) :12059-12068
[8]   An approach to the anhydride unit of CP-225,917 and CP-263,114 [J].
Clive, DLJ ;
Sun, SY ;
Gagliardini, V ;
Sano, MK .
TETRAHEDRON LETTERS, 2000, 41 (33) :6259-6263
[9]   Synthesis of tricyclic bridgehead olefins related to the core structure of CP-225,917 and CP-263,114 - solvent, strain, and substitution effects on siloxy-Cope rearrangements [J].
Clive, DLJ ;
Sun, SY ;
He, X ;
Zhang, JH ;
Gagliardini, V .
TETRAHEDRON LETTERS, 1999, 40 (25) :4605-4609
[10]  
Dabrah TT, 1997, J ANTIBIOT, V50, P1