Total synthesis of (+)-boronolide, (+)-deacetylboronolide, and (+)-dideacetylboronolide

被引:42
作者
Chandrasekhar, M [1 ]
Chandra, KL [1 ]
Singh, VK [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
关键词
D O I
10.1021/jo0269058
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Total synthesis of (+)-boronolide, (+)-deacetylboronolide, and (+)-dideacetylboronolide has been achieved from a single intermediate 26, which was synthesized in 11 steps from a D-mannitol-derived intermediate 8 in an overall yield of 10%. The key steps in the synthesis are inversion of a chiral center by taking an advantage of the inherent mechanism involved in the ring closing to an epoxide via intramolecular S(N)2 reaction and lactonization of a diol using Fetizons reagent. The strategy is amenable to preparation of analogues of (+)-boronolide in sufficient amount for further screening of biological activity.
引用
收藏
页码:4039 / 4045
页数:7
相关论文
共 39 条
[1]  
ADITYACHAUDHURY N, 1979, J SCI IND RES INDIA, V38, P265
[2]  
BROWN RCD, 1994, SYNLETT, P415
[3]   Stereoselective synthesis of (+)-boronolide [J].
Carda, M ;
Rodríguez, S ;
Segovia, B ;
Marco, JA .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (18) :6560-6563
[4]   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
[5]   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
[6]   Total synthesis of (-)- and (+)-lentiginosine [J].
Chandra, KL ;
Chandrasekhar, M ;
Singh, VK .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13) :4630-4633
[7]   Formal total synthesis of (+)-boronolide [J].
Chandrasekhar, M ;
Raina, S ;
Singh, VK .
TETRAHEDRON LETTERS, 2000, 41 (25) :4969-4971
[8]  
COSSY J, 1988, B SOC CHIM FR, P989
[9]  
Davies-Coleman M T, 1989, Fortschr Chem Org Naturst, V55, P1
[10]   STEREOCHEMICAL STUDIES ON BORONOLIDE, AN ALPHA-PYRONE FROM TETRADENIA-BARBERAE [J].
DAVIESCOLEMAN, MT ;
RIVETT, DEA .
PHYTOCHEMISTRY, 1987, 26 (11) :3047-3050