A double alkylation - ring closing metathesis approach to spiroimines

被引:34
作者
Brimble, MA [1 ]
Trzoss, M [1 ]
机构
[1] Univ Auckland, Dept Chem, Auckland 1, New Zealand
关键词
gymnodimi; spirolactams; beta-trimethylsilylethoxycarbonyl (TEOC);
D O I
10.1016/j.tet.2004.04.059
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
As part of a programme directed towards the synthesis of the marine toxins, the spirolides and gymnodimine, a convenient synthesis of the key bicyclic spiroimine ring systems has been developed. The method involves double alkylation of a simple lactam, Grubbs ring closing metathesis of the resultant dialkylated lactam then reduction of the lactam to an imine. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5613 / 5622
页数:10
相关论文
共 43 条
[31]   Reduction of secondary carboxamides to imines [J].
Schedler, DJA ;
Li, J ;
Ganem, B .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (12) :4115-4119
[32]  
Schuster M, 1997, ANGEW CHEM INT EDIT, V36, P2037
[33]   GYMNODIMINE, A NEW MARINE TOXIN OF UNPRECEDENTED STRUCTURE ISOLATED FROM NEW-ZEALAND OYSTERS AND THE DINOFLAGELLATE, GYMNODINIUM SP [J].
SEKI, T ;
SATAKE, M ;
MACKENZIE, L ;
KASPAR, HF ;
YASUMOTO, T .
TETRAHEDRON LETTERS, 1995, 36 (39) :7093-7096
[34]   New developments in the chemistry of N-acyliminium ions and related intermediates [J].
Speckamp, WN ;
Moolenaar, MJ .
TETRAHEDRON, 2000, 56 (24) :3817-3856
[35]   The absolute stereochemistry of the New Zealand shellfish toxin gymnodimine [J].
Stewart, M ;
Blunt, JW ;
Munro, MHG ;
Robinson, WT ;
Hannah, DJ .
TETRAHEDRON LETTERS, 1997, 38 (27) :4889-4890
[36]   Structural determination of pteriatoxins A, B and C, extremely potent toxins from the bivalve Pteria penguin [J].
Takada, N ;
Umemura, N ;
Suenaga, K ;
Uemura, D .
TETRAHEDRON LETTERS, 2001, 42 (20) :3495-3497
[37]   The development of L2X2Ru=CHR olefin metathesis catalysts:: An organometallic success story [J].
Trnka, TM ;
Grubbs, RH .
ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (01) :18-29
[38]   Synthesis of spirocyclic imines: Key pharmacophores in the shellfish toxins spirolides and gymnodimine [J].
Trzoss, M ;
Brimble, MA .
SYNLETT, 2003, (13) :2042-2046
[39]  
Tsujimoto T, 2002, SYNLETT, P399
[40]   PINNATOXIN-A - A TOXIC AMPHOTERIC MACROCYCLE FROM THE OKINAWAN BIVALVE PINNA-MURICATA [J].
UEMURA, D ;
CHOU, T ;
HAINO, T ;
NAGATSU, A ;
FUKUZAWA, S ;
ZHENG, SZ ;
CHEN, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (03) :1155-1156