Formal total synthesis of (+)-boronolide

被引:26
作者
Chandrasekhar, M [1 ]
Raina, S [1 ]
Singh, VK [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
关键词
D O I
10.1016/S0040-4039(00)00749-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(+)-Boronolide, a polyacetoxy natural product having four contiguous asymmetric centers has been synthesized from D-mannitol. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4969 / 4971
页数:3
相关论文
共 13 条
[1]   SYNTHESIS OF SUBSTITUTED 5,6-DIHYDRO-2H-PYRAN-2-ONES - PROPIOLIC ACID DIANION AS A REACTIVE 3-CARBON NUCLEOPHILE [J].
CARLSON, RM ;
OYLER, AR ;
PETERSON, JR .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (11) :1610-1616
[2]   A PRACTICAL ROUTE TOWARDS ALPHA,BETA-UNSATURATED DELTA-LACTONES BASED ON A [3+3] STRATEGY - SYNTHESIS OF (-)-ARGENTILACTONE [J].
CARRETERO, JC ;
GHOSEZ, L .
TETRAHEDRON LETTERS, 1988, 29 (17) :2059-2062
[3]   STEREOCHEMICAL STUDIES ON BORONOLIDE, AN ALPHA-PYRONE FROM TETRADENIA-BARBERAE [J].
DAVIESCOLEMAN, MT ;
RIVETT, DEA .
PHYTOCHEMISTRY, 1987, 26 (11) :3047-3050
[4]  
FRANCA NC, 1971, CR ACAD SCI C CHIM, V273, P439
[5]   A stereoselective synthesis of (+)-boronolide [J].
Ghosh, AK ;
Bilcer, G .
TETRAHEDRON LETTERS, 2000, 41 (07) :1003-1006
[6]   Enantiocontrolled synthesis of (+)-boronolide [J].
Honda, T ;
Horiuchi, S ;
Mizutani, H ;
Kanai, K .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (15) :4944-4948
[7]   THE SYNTHESIS OF BORONOLIDE [J].
JEFFORD, CW ;
MOULIN, MC .
HELVETICA CHIMICA ACTA, 1991, 74 (02) :336-342
[8]  
KJAER A, 1985, ACTA CHEM SCAND B, V39, P745
[9]   SYNTHESIS OF (+)-BORONOLIDE FROM D-GLUCOSE [J].
NAGANO, H ;
YASUI, H .
CHEMISTRY LETTERS, 1992, (06) :1045-1048
[10]   Asymmetric synthesis of 5-hexadecanolide, pheromone of the queen of the Oriental hornet, Vespa orientalis [J].
Raina, S ;
Singh, VK .
TETRAHEDRON, 1996, 52 (12) :4479-4484