Asymmetric synthesis of seven-carbon segments of the phorboxazoles and (-)-discodermolide:: Complementary route from racemic trans-2,4-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one

被引:63
作者
Misske, AM [1 ]
Hoffmann, HMR [1 ]
机构
[1] Leibniz Univ Hannover, Dept Organ Chem, D-30167 Hannover, Germany
关键词
D O I
10.1016/S0040-4020(99)00127-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The C20-C26 segment of the phorboxazoles A and B and the C1-C7 segment of (-)-discodermolide were synthesized in excellent chemical and optical yield using trans-2,4-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one rac-1 with four stereogenic centres and three prostereogenic sp(2)-sites as an early racemic switch. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4315 / 4324
页数:10
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共 47 条
[1]   Convergent synthesis of the C31-C46 domain of the phorboxazole natural products [J].
Ahmed, F ;
Forsyth, CJ .
TETRAHEDRON LETTERS, 1998, 39 (3-4) :183-186
[2]   Stereoselective synthesis of the C3-C17 bis-oxane domain of phorboxazole A [J].
Cink, RD ;
Forsyth, CJ .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :5672-5673
[3]   STUDIES ON THE ALKYLATION OF CHIRAL ENOLATES - APPLICATION TOWARD THE TOTAL SYNTHESIS OF DISCODERMOLIDE [J].
CLARK, DL ;
HEATHCOCK, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) :5878-5879
[4]   8-Oxabicyclo[3.2.1]oct-6-en-3-one as a module for the synthesis of beta-alkoxy-delta-valerolactones relevant to natural products and drugs [J].
Dunkel, R ;
Mentzel, M ;
Hoffmann, HMR .
TETRAHEDRON, 1997, 53 (44) :14929-14936
[5]   TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC LONOMYCIN-A (EMERICID) [J].
EVANS, DA ;
RATZ, AM ;
HUFF, BE ;
SHEPPARD, GS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (12) :3448-3467
[6]   Enantioselective synthesis of altohyrtin C (spongistatin 2):: Fragment assembly and revision of the spongistatin 2 stereochemical assignment [J].
Evans, DA ;
Trotter, BW ;
Côté, B ;
Coleman, PJ ;
Dias, LC ;
Tyler, AN .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (24) :2744-2747
[7]   Enantioselective synthesis of altohyrtin C (spongistatin 2):: Synthesis of the EF-bis(pyran) subunit [J].
Evans, DA ;
Trotter, BW ;
Côté, B ;
Coleman, PJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (24) :2741-2744
[8]   Enantioselective synthesis of altohyrtin C (spongistatin 2): Synthesis of the AB- and CD-spiroketal subunits [J].
Evans, DA ;
Coleman, PJ ;
Dias, LC .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (24) :2738-2741
[9]   THE SYNTHESIS OF A C-9-C-17 FRAGMENT OF DISCODERMOLIDE [J].
EVANS, PL ;
GOLEC, JMC ;
GILLESPIE, RJ .
TETRAHEDRON LETTERS, 1993, 34 (50) :8163-8166
[10]   Total synthesis of phorboxazole A [J].
Forsyth, CJ ;
Ahmed, F ;
Cink, RD ;
Lee, CS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (22) :5597-5598