Synthesis of chiral 4-hydroxy-2,3-unsaturated carbonyl compounds from 3,4-epoxy alcohols by oxidation: application in the formal synthesis of macrosphelide A

被引:23
作者
Chakraborty, TK [1 ]
Purkait, S [1 ]
Das, S [1 ]
机构
[1] Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India
关键词
epoxy alcohols; Sharpless epoxidation; epoxide opening; macrosphelides;
D O I
10.1016/j.tet.2003.09.070
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An interesting transformation during the oxidation of 3,4-epoxy alcohols 1a-d, derived from the corresponding homoallylic alcohols, led to the formation of 4-hydroxy-2,3-unsaturated carbonyls 2a-d in very good yields. One of these products 2c was transformed into the functionalised carboxylic acid 5, an advanced stage intermediate from which the total synthesis of macrosphelide A has been reported. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9127 / 9135
页数:9
相关论文
共 37 条
[1]   σ-π chelation-controlled chemoselective ring openings of epoxides [J].
Asao, N ;
Kasahara, T ;
Yamamoto, Y .
TETRAHEDRON LETTERS, 2001, 42 (44) :7903-7905
[2]  
Awakura D, 2000, SYNLETT, P1733
[3]   Copper(II) tetrafluoroborate catalyzed ring-opening reaction of epoxides with alcohols at room temperature [J].
Barluenga, J ;
Vázquez-Villa, H ;
Ballesteros, A ;
González, JM .
ORGANIC LETTERS, 2002, 4 (17) :2817-2819
[4]  
Brandes BD, 2001, SYNLETT, P1013
[5]   Studies directed toward the syntheses of amphidinolides: formal total synthesis of (-)-amphidinolide P [J].
Chakraborty, TK ;
Das, S .
TETRAHEDRON LETTERS, 2001, 42 (19) :3387-3390
[6]   Convenient preparation of ytterbium(III) chalcogenolate complexes by insertion of ytterbium into chalcogen-chalcogen bonds. Application in the ring-opening of epoxides [J].
Dowsland, J ;
McKerlie, F ;
Procter, DJ .
TETRAHEDRON LETTERS, 2000, 41 (25) :4923-4927
[7]   New members of the macrosphelides from Microsphaeropsis sp FO-5050IV [J].
Fukami, A ;
Taniguchi, Y ;
Nakamura, T ;
Rho, MC ;
Kawaguchi, K ;
Hayashi, M ;
Komiyama, K ;
Omura, S .
JOURNAL OF ANTIBIOTICS, 1999, 52 (05) :501-504
[8]  
FURUMAI T, 1968, ANTIBIOT, V21, P85
[9]   CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].
GAO, Y ;
HANSON, RM ;
KLUNDER, JM ;
KO, SY ;
MASAMUNE, H ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780
[10]   Macrosphelide, a novel inhibitor of cell-cell adhesion molecule .1. Taxonomy, fermentation, isolation and biological activities [J].
Hayashi, M ;
Kim, YP ;
Hiraoka, H ;
Natori, M ;
Takamatsu, S ;
Kawakubo, T ;
Masuma, R ;
Komiyama, K ;
Omura, S .
JOURNAL OF ANTIBIOTICS, 1995, 48 (12) :1435-1439