Preliminary feasibility studies on total synthesis of the unusual marine bryozoan alkaloids chartellamide A and B

被引:32
作者
Pinder, JL [1 ]
Weinreb, SM [1 ]
机构
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
基金
美国国家科学基金会;
关键词
Staudinger cycloadditions; azetidinones; imines; alkaloids; marine metabolites;
D O I
10.1016/S0040-4039(03)00876-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A strategy for synthesis of the chartellamide marine alkaloids has been tested in a model, leading to the polycyclic ring system of the natural product. but which unfortunately does not provide the requisite C-9,20 relative stereochemistry. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4141 / 4143
页数:3
相关论文
共 15 条
[1]   Beta-lactams derived from the reaction of phenanthridines and 11H-dibenzo[b,e]azepin-11-one with phenylvaleryl chloride.: Synthesis of fused analogs of the cholesterol absorption inhibitor Sch 48461. [J].
Afonso, A ;
Rosenblum, SB ;
Puar, MS ;
McPhail, AT .
TETRAHEDRON LETTERS, 1998, 39 (41) :7431-7434
[2]   CHARTELLAMIDE-A AND CHARTELLAMIDE-B, HALOGENATED BETA-LACTAM INDOLE IMIDAZOLE ALKALOIDS FROM THE MARINE BRYOZOAN CHARTELLA-PAPYRACEA [J].
ANTHONI, U ;
BOCK, K ;
CHEVOLOT, L ;
LARSEN, C ;
NIELSEN, PH ;
CHRISTOPHERSEN, C .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (25) :5638-5639
[3]   MARINE ALKALOIDS .12. CHARTELLINES, HALOGENATED BETA-LACTAM ALKALOIDS FROM THE MARINE BRYOZOAN CHARTELLA-PAPYRACEA [J].
ANTHONI, U ;
CHEVOLOT, L ;
LARSEN, C ;
NIELSEN, PH ;
CHRISTOPHERSEN, C .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (21) :4709-4712
[4]   Synthesis of functionalized olefins by cross and ring-closing metatheses [J].
Chatterjee, AK ;
Morgan, JP ;
Scholl, M ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (15) :3783-3784
[5]   MARINE ALKALOIDS .10. CHARTELLINE-A - A PENTAHALOGENATED ALKALOID FROM THE MARINE BRYOZOAN CHARTELLA-PAPYRACEA [J].
CHEVOLOT, L ;
CHEVOLOT, AM ;
GAJHEDE, M ;
LARSEN, C ;
ANTHONI, U ;
CHRISTOPHERSEN, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (15) :4542-4543
[6]   A NEW EFFICIENT ACCESS TO CYCLIC IMINES [J].
LAMBERT, PH ;
VAULTIER, M ;
CARRIE, R .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (21) :1224-1225
[7]  
LIN X, 2002, THESIS PENNSYLVANIA
[8]   Model studies on total synthesis of the chartellines, spirocyclic β-lactam alkaloids from a marine bryozoan [J].
Lin, XC ;
Weinreb, SM .
TETRAHEDRON LETTERS, 2001, 42 (14) :2631-2633
[9]   MARINE ALKALOIDS .14. PROTOTROPY OF CHARTELLINES FROM CHARTELLA-PAPYRACEA [J].
NIELSEN, PH ;
ANTHONI, U ;
CHRISTOPHERSEN, C .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1988, 42 (07) :489-491
[10]  
Palomo C, 1999, EUR J ORG CHEM, V1999, P3223