Oxidative fragmentation of bicyclic hydroxy silanes and stannanes: a strategy for the stereoselective synthesis of kainoids

被引：8

作者：

Clayden, Jonathan ^{[1
]}

Hebditch, Katherine R. ^{[1
]}

Read, Benjamin ^{[1
]}

Helliwell, Madeleine ^{[1
]}

机构：

[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 48期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/j.tetlet.2007.09.150

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of tin or silicon nucleophiles to bicyclic enones generated by dearomatising cyclisation gives starmanes and silanes stereo selectively. These compounds may be fragmented under oxidative conditions to generate substituted pyrrolidines bearing C2 and C3 substituents closely related to those found in the kainoid series of cyclic amino acids. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：8550 / 8553

页数：4

共 18 条

[1] Synthesis of a potent (±)-4-(2-hydroxyphenyl) analogue of the acromelic acids by dearomatising cyclisation of a lithiated N-p-methoxybenzyl-4-methoxy-l-naphthamide [J].

Ahmed, A ;

Bragg, RA ;

Clayden, J ;

Tchabanenko, K .

TETRAHEDRON LETTERS, 2001, 42 (20) :3407-3410

[2] CARBOCYCLIC RING EXPANSION REACTIONS VIA RADICAL CHAIN PROCESSES [J].

BALDWIN, JE ;

ADLINGTON, RM ;

ROBERTSON, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (21) :1404-1406

[3] Chemistry of domoic acid, isodomoic acids, and their analogues [J].

Clayden, J ;

Read, B ;

Hebditch, KR .

TETRAHEDRON, 2005, 61 (24) :5713-5724

[4] The synthesis of (-)-isodomoic acid C [J].

Clayden, J ;

Knowles, FE ;

Baldwin, IR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (08) :2412-2413

[5] Synthesis of α-methyl kainic acid by stereospecific lithiation-dearomatizing cyclization of a chiral benzamide [J].

Clayden, J ;

Knowles, FE ;

Menet, CJ .

TETRAHEDRON LETTERS, 2003, 44 (16) :3397-3400

[6] Synthesis of (-)-kainic acid using chiral lithium amides in an asymmetric dearomatizing cyclization [J].

Clayden, J ;

Menet, CJ ;

Tchabanenko, K .

TETRAHEDRON, 2002, 58 (23) :4727-4733

[7] Dearomatizing anionic cyclization of substituted N-cumyl-N-benzylbenzamides on treatment with LDA:: Synthesis of partially saturated substituted isoindolones [J].

Clayden, J ;

Menet, CJ ;

Mansfield, DJ .

ORGANIC LETTERS, 2000, 2 (26) :4229-4232

[8] Synthesis of (±)-kainic acid by dearomatising cyclisation of a lithiated N-benzyl p-anisamide [J].

Clayden, J ;

Tchabanenko, K .

CHEMICAL COMMUNICATIONS, 2000, (04) :317-318

[9]

CLAYTON J, 2004, STRATEGIES TACTIES O, P72

[10] CONJUGATE ADDITION OF THE PHENYLDIMETHYLSILYL GROUP TO ALPHA-BETA-UNSATURATED CARBONYL-COMPOUNDS USING A SILYLZINCATE IN-PLACE OF THE SILYLCUPRATE [J].

CRUMP, RANC ;

FLEMING, I ;

URCH, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (06) :701-706

← 1 2 →