Biomimetic studies towards the C28-C40 polycyclic domain of the azaspiracids

被引:38
作者
Aiguade, J [1 ]
Hao, JL [1 ]
Forsyth, CJ [1 ]
机构
[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(00)02156-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An acyclic intermediate representing a putative biomimetic precursor of the C28-C40 domain of the novel marine toxin azaspiracid was constructed convergently from C28-C34 and C35-C40 fragments. In studying the assembly of the C28-C34 dioxabicyclo[3.3.1]nonane system via an intramolecular hetero-conjugate addition upon a C34-C36 enone, a stereoselective C-Michael addition intervened to provide a highly substituted cyclohexane. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:817 / 820
页数:4
相关论文
共 20 条
[1]   CONVENIENT GENERAL-METHOD FOR THE PREPARATION OF PRIMARY ALKYLLITHIUMS BY LITHIUM IODINE EXCHANGE [J].
BAILEY, WF ;
PUNZALAN, ER .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (19) :5404-5406
[2]   HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].
BLANCHETTE, MA ;
CHOY, W ;
DAVIS, JT ;
ESSENFELD, AP ;
MASAMUNE, S ;
ROUSH, WR ;
SAKAI, T .
TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186
[3]   SYNTHESIS OF THE POLYETHER ANTIBIOTIC MONENSIN .3. COUPLING OF PRECURSORS AND TRANSFORMATION TO MONENSIN [J].
COLLUM, DB ;
MCDONALD, JH ;
STILL, WC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (06) :2120-2121
[4]   REDUCTIVE CLEAVAGE OF TERT-BUTYLDIMETHYLSILYL ETHERS BY DIISOBUTYLALUMINUM HYDRIDE [J].
COREY, EJ ;
JONES, GB .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) :1028-1029
[5]  
deNooy AEJ, 1996, SYNTHESIS-STUTTGART, P1153
[6]   A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287
[7]   ASYMMETRIC ALKYLATION REACTIONS OF CHIRAL IMIDE ENOLATES - A PRACTICAL APPROACH TO THE ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED CARBOXYLIC-ACID DERIVATIVES [J].
EVANS, DA ;
ENNIS, MD ;
MATHRE, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (06) :1737-1739
[8]   Carbon-carbon bond formations involving organochromium(III) reagents [J].
Fürstner, A .
CHEMICAL REVIEWS, 1999, 99 (04) :991-1045
[9]   Multiple organ damage caused by a new toxin azaspiracid, isolated from mussels produced in Ireland [J].
Ito, E ;
Satake, M ;
Ofuji, K ;
Kurita, N ;
McMahon, T ;
James, K ;
Yasumoto, T .
TOXICON, 2000, 38 (07) :917-930
[10]   Formal total syntheses of the beta-lactam antibiotics thienamycin and PS-5 [J].
Jacobi, PA ;
Murphree, S ;
Rupprecht, F ;
Zheng, WJ .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) :2413-2427