Formal syntheses of (+/-)-pinnaic acid and (+/-)-halichlorine

被引:46
作者
Andrade, RB [1 ]
Martin, SF [1 ]
机构
[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA
关键词
D O I
10.1021/ol0525009
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Concise formal syntheses of marine alkaloids (+/-)-pinnaic acid (1) and (+/-)-halichlorine (2) have been accomplished from a common intermediate. The syntheses illustrate the utility of selective olefin cross metathesis methodologies for the elaboration of advanced synthetic intermediates in complex molecule synthesis.
引用
收藏
页码:5733 / 5735
页数:3
相关论文
共 51 条
[1]   Synthesis of pinnaic acid; Asymmetric construction of spirocyclic core [J].
Arimoto, H ;
Asano, S ;
Uemura, D .
TETRAHEDRON LETTERS, 1999, 40 (18) :3583-3586
[2]   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
[3]   Recent advances in the Baylis-Hillman reaction and applications [J].
Basavaiah, D ;
Rao, AJ ;
Satyanarayana, T .
CHEMICAL REVIEWS, 2003, 103 (03) :811-891
[4]   Enantioselective synthesis of (+)-anatoxin-a via enyne metathesis [J].
Brenneman, JB ;
Machauer, R ;
Martin, SF .
TETRAHEDRON, 2004, 60 (34) :7301-7314
[5]  
CARLOS TM, 1994, BLOOD, V84, P2068
[6]  
Carson MW, 2001, ANGEW CHEM INT EDIT, V40, P4450, DOI 10.1002/1521-3773(20011203)40:23<4450::AID-ANIE4450>3.0.CO
[7]  
2-M
[8]  
Carson MW, 2001, ANGEW CHEM INT EDIT, V40, P4453, DOI 10.1002/1521-3773(20011203)40:23<4453::AID-ANIE4453>3.0.CO
[9]  
2-4
[10]   A general model for selectivity in olefin cross metathesis [J].
Chatterjee, AK ;
Choi, TL ;
Sanders, DP ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) :11360-11370