Synthesis of a spirocyclic amine related to the marine natural products halichlorine and pinnaic acid

被引:18
作者
Clive, DLJ [1 ]
Wang, H [1 ]
Yu, ML [1 ]
机构
[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
halichlorine pinnaic acid; ring closing metathesis; spiro compound; Wittig homologation;
D O I
10.1016/j.tetlet.2005.02.133
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The bis-ester 5 was elaborated into tricyclic lactam 8, which has previously been converted into the spirotricyclic amine 9, a compound that represents a large portion of the marine natural product halichlorine. (c) 2005 Published by Elsevier Ltd.
引用
收藏
页码:2853 / 2855
页数:3
相关论文
共 22 条
[1]   Combining two-directional synthesis and tandem reactions. Part 4: A concise approach to the spirocyclic core of halichlorine and the pinnaic acids [J].
Arini, LG ;
Szeto, P ;
Hughes, DL ;
Stockman, RA .
TETRAHEDRON LETTERS, 2004, 45 (45) :8371-8374
[2]   SIMPLE SYNTHESIS OF A C-2 SYMMETRICAL VICINAL DIAMINE - HIGHLY DIASTEREOSELECTIVE GRIGNARD ADDITION TO A CHIRAL BIS-IMINE [J].
BAMBRIDGE, K ;
BEGLEY, MJ ;
SIMPKINS, NS .
TETRAHEDRON LETTERS, 1994, 35 (20) :3391-3394
[3]  
Carson MW, 2001, ANGEW CHEM INT EDIT, V40, P4450, DOI 10.1002/1521-3773(20011203)40:23<4450::AID-ANIE4450>3.0.CO
[4]  
2-M
[5]  
Carson MW, 2001, ANGEW CHEM INT EDIT, V40, P4453, DOI 10.1002/1521-3773(20011203)40:23<4453::AID-ANIE4453>3.0.CO
[6]  
2-4
[7]   Total synthesis of (±)-halichlorine, (±)-pinnaic acid, and (±)-tauropinnaic acid [J].
Christie, HS ;
Heathcock, CH .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (33) :12079-12084
[8]   Synthesis of functionalized 1-azaspirocyclic cyclopentanones using Bronsted acid or N-bromosuccinimide promoted ring expansions [J].
Dake, GR ;
Fenster, MDB ;
Hurley, PB ;
Patrick, BO .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5668-5675
[9]   Alkynyliodonium salts in organic synthesis.: Application to the preparation of the tricyclic core of (±)-halichlorine [J].
Feldman, KS ;
Perkins, AL ;
Masters, KM .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23) :7928-7932
[10]   NOVEL REAGENT SYSTEM FOR CONVERTING A HYDROXY-GROUP INTO AN IODO-GROUP IN CARBOHYDRATES WITH INVERSION OF CONFIGURATION .2. [J].
GAREGG, PJ ;
SAMUELSSON, B .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (12) :2866-2869