Stereoselective synthesis of all four isomers of coronamic acid: A general approach to 3-methanoamino acids

被引:88
作者
Charette, AB
Cote, B
机构
[1] Departement de Chimie, Universite de Montreal, H3C 3J7., Quebec
关键词
D O I
10.1021/ja00156a009
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A general approach to the synthesis of enantiomerically enriched 3-methanoamino acids is presented where the cyclopropyl unit was introduced by a stereoselective cyclopropanation using a D-glucose-derived chiral auxiliary. This methodology was applied to the synthesis of the four stereoisomers of coronamic acid 14, 17, 20, and 22. Starting with the readily available allylic alcohol 5, beta-D-glucopyranoses (E)-6 and (E)-7 have been selectively prepared using trichloroacetimidate 2. These olefins were cyclopropanated with very high diastereoselectivities using Et(2)Zn/CH2I2 (greater than or equal to 98% de) and Et(2)Zn/CH2ICI (greater than or equal to 97% de) in yields greater than 90%. After cleavage of the chiral auxiliary by ring contraction of the 2 O-triflyl derivative of cyclopropanes 8 and 9, cyclopropylmethanols (-)-10 and (+)-11 have been transformed to all four isomeric protected amino acids by selective protecting group manipulations, oxidation of primary alcohols, and Curtius rearrangement.
引用
收藏
页码:12721 / 12732
页数:12
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共 100 条
  • [1] KMNO4 REVISITED - OXIDATION OF ALDEHYDES TO CARBOXYLIC-ACIDS IN THE TERT-BUTYL ALCOHOL AQUEOUS NAH2PO4 SYSTEM
    ABIKO, A
    ROBERTS, JC
    TAKEMASA, T
    MASAMUNE, S
    [J]. TETRAHEDRON LETTERS, 1986, 27 (38) : 4537 - 4540
  • [3] ON THE BIOSYNTHESIS OF ETHYLENE
    ADLINGTON, RM
    APLIN, RT
    BALDWIN, JE
    RAWLINGS, BJ
    OSBORNE, D
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (18) : 1086 - 1087
  • [4] INHIBITION OF PIG-KIDNEY L-AROMATIC AMINO-ACID DECARBOXYLASE BY 2,3-METHANO-META-TYROSINES
    AHMAD, S
    PHILLIPS, RS
    STAMMER, CH
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (08) : 1410 - 1417
  • [5] ALAMI A, 1993, B SOC CHIM FR, V130, P5
  • [6] ASYMMETRIC-SYNTHESIS OF CIS AND TRANS-2-METHYL-1-AMINOCYCLOPROPANECARBOXYLIC ACIDS AND 2-ETHYL-1-AMINOCYCLOPROPANECARBOXYLIC ACIDS
    ALAMI, A
    CALMES, M
    DAUNIS, J
    ESCALE, F
    JACQUIER, R
    ROUMESTANT, ML
    VIALLEFONT, P
    [J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (03) : 175 - 178
  • [7] ENANTIOSELECTIVE SYNTHESIS OF (+)-(1R,2S)-ALLOCORONAMIC ACID
    ALCARAZ, C
    HERRERO, A
    MARCO, JL
    FERNANDEZALVAREZ, E
    BERNABE, M
    [J]. TETRAHEDRON LETTERS, 1992, 33 (38) : 5605 - 5608
  • [8] [Anonymous], [No title captured], Patent No. [2155113A1, 2155113]
  • [9] ARENAL I, 1983, AN QUIM C-ORG BIOQ, V79, P65
  • [10] ARIENTEFLICHE C, 1992, SYNTHETIC COMMUN, V22, P1155