Ring closing metathesis for the formation of medium ring ethers: the total synthesis of (-)-isolaurallene

被引:63
作者
Crimmins, MT [1 ]
Emmitte, KA [1 ]
Choy, AL [1 ]
机构
[1] Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
基金
美国国家卫生研究院;
关键词
marine natural products; isolaurallene; metathesis; asymmetric aldol; asymmetric alkylation; oxonene;
D O I
10.1016/S0040-4020(02)00040-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total synthesis of the marine metabolite (-)-isolaurallene is described. Two approaches to the core nine-membered ether are presented both of which are based on a ring closing metathesis to close the cyclic ether. (C) 2002 Published by Elsevier Science Ltd.
引用
收藏
页码:1817 / 1834
页数:18
相关论文
共 48 条
[1]   ZNBR2-MEDIATED HIGHLY DIASTEREOSELECTIVE ADDITION OF GRIGNARD-REAGENTS TO ALPHA-BENZYLOXY ALDEHYDES [J].
ASAMI, M ;
KIMURA, R .
CHEMISTRY LETTERS, 1985, (08) :1221-1222
[2]   CHIRAL SYNTHESIS VIA ORGANOBORANES .24. B-ALLYLBIS(2-ISOCARANYL)BORANE AS A SUPERIOR REAGENT FOR THE ASYMMETRIC ALLYLBORATION OF ALDEHYDES [J].
BROWN, HC ;
RANDAD, RS ;
BHAT, KS ;
ZAIDLEWICZ, M ;
RACHERLA, US .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (06) :2389-2392
[3]  
Clark JS, 2000, ANGEW CHEM INT EDIT, V39, P372, DOI 10.1002/(SICI)1521-3773(20000117)39:2<372::AID-ANIE372>3.0.CO
[4]  
2-Y
[5]   Total synthesis of (+)-laurencin: An asymmetric alkylation-ring-closing metathesis approach to medium ring ethers [J].
Crimmins, MT ;
Emmitte, KA .
ORGANIC LETTERS, 1999, 1 (12) :2029-2032
[6]  
Crimmins MT, 2000, SYNTHESIS-STUTTGART, P899
[7]   Asymmetric aldol additions:: Use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones [J].
Crimmins, MT ;
King, BW ;
Tabet, EA ;
Chaudhary, K .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) :894-902
[8]   Asymmetric total synthesis of (-)-isolaurallene [J].
Crimmins, MT ;
Emmitte, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (07) :1533-1534
[9]   An improved synthetic preparation of 3-butenal [J].
Crimmins, MT ;
Kirincich, SJ ;
Wells, AJ ;
Choy, AL .
SYNTHETIC COMMUNICATIONS, 1998, 28 (19) :3675-3679
[10]   An asymmetric aldol-ring-closing metathesis strategy for the enantioselective construction of oxygen heterocycles: An efficient approach to the enantioselective synthesis of (+)-laurencin [J].
Crimmins, MT ;
Choy, AL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (24) :5653-5660