SYNTHESIS OF ENANTIOMERIC PYRANS FROM A 3-O-ALLYLALLOSE DERIVATIVE BY THE APPLICATION OF INTRAMOLECULAR NITRONE CYCLOADDITION

被引:17
作者
BHATTACHARJEE, A
BHATTACHARJYA, A
PATRA, A
机构
[1] INDIAN INST CHEM BIOL,CALCUTTA 700032,W BENGAL,INDIA
[2] UNIV CALCUTTA,UNIV COLL SCI,DEPT CHEM,CTR ADV STUDIES NAT PROD,CALCUTTA 700009,W BENGAL,INDIA
关键词
D O I
10.1016/0040-4039(95)00832-W
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The intramolecular nitrone cycloaddition of three sets of 3-O-allylpyranose and the corresponding homochiral 3-O-allylfuranose-5-aldehyde derivatives was studied; one set derived from D-allose gave rise to only pyran derivatives which were converted to enantiomeric pyranoisoxazolidines via minor degradations.
引用
收藏
页码:4677 / 4680
页数:4
相关论文
共 11 条
  • [1] Datta, Chattopadhyay, Mukhopadhyay, Bhattacharjya, Tetrahedron Lett., 34, (1993)
  • [2] Collins, Ashwood, Eder, Wright, Kennedy, Tetrahedron Lett., 31, (1990)
  • [3] Bhattacharjya, Chattopadhyay, McPhail, McPhail, Intramolecular 1,3-dipolar cycloaddition of a nitrone derived from 3-O-allyl-D-(+)-glucose: an expedient synthesis of a chiral oxepane derivative, Journal of the Chemical Society, Chemical Communications, (1990)
  • [4] Bhattacharjya, Chattopadhyay, McPhail, McPhail, corrigendum, Journal of the Chemical Society, Chemical Communications, (1991)
  • [5] Shing, Fung, Wong, Ring-selective syntheses of homochiral oxepanes and tetrahydropyrans from carbohydrates via intramolecular nitrone or nitrile oxide cycloadditions, Journal of the Chemical Society, Chemical Communications, (1994)
  • [6] Baker, Horton, Tindall, Carbohydr. Res., 24, (1972)
  • [7] Brimacombe, Rollins, Thompson, Carbohydr. Res., 31, (1973)
  • [8] Funabashi, Sato, Yoshimura, Bull. Chem. Soc. Jpn., 49, (1976)
  • [9] Presented at the “Fifteenth National Symposium on Organic Chemistry” (NASOC-XV), (1994)
  • [10] “Tenth International Congress on Organic Synthesis” (ICOS-10), (1994)