A short and efficient synthesis of 2R,3R,4R-3,4-dihydroxyproline, 1,4-dideoxy-1,4-imino-L-xylitol, 2R,3R,4R,5S-3,4,5-trihydroxypipecolic acid, and 1,5-dideoxy-1,5-imino-L-iditol

被引：0
|
作者：
Lee, BW [1 ]
Jeong, IY [1 ]
Yang, MS [1 ]
Choi, SU [1 ]
Park, KH [1 ]
机构：
[1] Gyeongsang Natl Univ, Dept Agr Chem, Chinju 660701, South Korea
来源：
SYNTHESIS-STUTTGART | 2000年 / 09期
关键词：
carbohydrates; iodine; amino acids; one-pot cyclization; azasugars; protecting group;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The syntheses of pyrrolidine alkaloids (-)-1 and (+)-3 were accomplished in 47% and 60% overall yield from 2-azido-2-deoxy-L-idonate 5, while piperidine alkaloids (-)-2 and (+)-4 were obtained in 51% acid 53% overall yield from the same starting material. Key step includes iodine promoted one-pot cyclization, and selective deprotection of isopropylidene and 9-phenylfluoren-9-yl (Pf) group.
引用
收藏
页码：1305 / 1309
页数：5
相关论文
共 50 条
  • [21] Short and efficient synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-tetrahydroxyazepanes via the Henry reaction
    Chakraborty, C
    Dhavale, DD
    CARBOHYDRATE RESEARCH, 2006, 341 (07) : 912 - 917
  • [22] A new asymmetric synthesis of (2S,3R,4R,5S)-trihydroxypipecolic acid
    Tsimilaza, Andriamihamina
    Tite, Tony
    Boutefnouchet, Sabrina
    Lallemand, Marie-Christine
    Tillequin, Francois
    Husson, Henri-Philippe
    TETRAHEDRON-ASYMMETRY, 2007, 18 (13) : 1585 - 1588
  • [23] THE SYNTHESIS OF (2R,3S)-(2S,3R) [4-C-14]AGARIC ACID AND (2R,3R)-(2S-3S) [4,4,5,5-H-3]AGARIC ACID
    LELLOUCHE, JP
    BEAUCOURT, JP
    PICHAT, L
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1984, 21 (02): : 125 - 132
  • [24] TOTAL SYNTHESES OF 1,5-DIDEOXY-1,5-IMINO-D-ERYTHRO-L-ALLO-OCTITOL AND (1S,2R,6R,7R,8S,8AS)-PENTAHYDROXYINDOLIZIDINE
    CHEN, YW
    VOGEL, P
    TETRAHEDRON LETTERS, 1992, 33 (34) : 4917 - 4920
  • [25] Synthesis of (2R,3R)-1,4-Dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol
    Bischop, Martina
    Cmrecki, Vesna
    Ophoven, Vera
    Pietruszka, Joerg
    SYNTHESIS-STUTTGART, 2008, (15): : 2488 - 2490
  • [26] SYNTHESIS OF (S,S)-DIISOPROPYL TARTRATE (E)-CROTYLBORONATE AND ITS REACTION WITH ALDEHYDES: (2R,3R,4R)-1,2-DIDEOXY-2-ETHENYL-4,5-O-(1-METHYLETHYLIDENE)-XYLITOL
    Sun, Huikai
    Roush, William R.
    ORGANIC SYNTHESES, 2011, 88 : 181 - +
  • [27] Studies on the transformation of nitrosugars into iminosugars III: synthesis of (2R,3R,4R,5R,6R)-2-(hydroxymethyl)azepane-3,4,5,6-tetraol and (2R,3R,4R,5R,6S)-2-(hydroxymethyl)azepane-3,4,5,6-tetraol
    Estevez, Amalia M.
    Soengas, Raquel G.
    Otero, Jose M.
    Estevez, Juan C.
    Nash, Robert J.
    Estevez, Ramon J.
    TETRAHEDRON-ASYMMETRY, 2010, 21 (01) : 21 - 26
  • [28] SYNTHESIS OF (2S,3R,4R)-3,4-DIHYDROXYPROLINE FROM 2,5-DIBROMO-2,5-DIDEOXY-D-XYLONO-1,4-LACTONE OR 2,5-DIBROMO-2,5-DIDEOXY-D-LYXONO-1,4-LACTONE
    BOLS, M
    LUNDT, I
    ACTA CHEMICA SCANDINAVICA, 1992, 46 (03): : 298 - 300
  • [29] Synthetic studies on homophymine A: stereoselective synthesis of (2R,3R,4R,6R)-3-hydroxy-2,4,6-trimethyloctanoic acid
    Bellotta, Filomena
    D'Auria, Maria Valeria
    Sepe, Valentina
    Zampella, Angela
    TETRAHEDRON, 2009, 65 (18) : 3659 - 3663
  • [30] SYNTHESIS OF (2R,3R,4R,5R)-3,4-DIHYDROXY-2,5-DIHYDROXYMETHYLPYRROLIDINE AND (-)-ANISOMYCIN DERIVATIVE FROM (S)-PYROGLUTAMIC ACID-DERIVATIVE
    IKOTA, N
    HETEROCYCLES, 1995, 41 (05) : 983 - 994
12345