Total synthesis of (4R,5S,6E,14S)- and (4R,5S,6E,14R)-cystothiazoles F

被引：5
|
作者：
Akita, Hiroyuki
Iwaki, Yuki
Kato, Keisuke
Qi, Jianhua
Ojika, Makoto
机构：
[1] Toho Univ, Sch Pharmaceut Sci, Funabashi, Chiba 2748510, Japan
[2] Novartis Pharma KK, Res Inst, Tsukuba, Ibaraki 3002611, Japan
[3] Nagoya Univ, Grad Sch Bioagricultural Sci, Chikusa Ku, Nagoya, Aichi 4648601, Japan
来源：
TETRAHEDRON-ASYMMETRY | 2007年 / 18卷 / 04期
关键词：
D O I：
10.1016/j.tetasy.2007.02.011
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Total synthesis of (4R,5S,6E,14S)- and (4R,5S,6E,14R)-cystothiazoles F 3 was achieved from the chiral bithiazole-type primary alcohols [(S)- and (R)-4-ethoxycarbonyl-2'-(1-hydroxymethylethyl)-2,4'-bithiazoles 8], which were obtained based on the enzymatic resolution of racemic alcohol 8 and its acetate 9. From a direct comparison by means of chiral HPLC between natural cystothiazole F 3 and synthetic compounds [(4R,5S,6E,14S)- and (4R,5S,6E,14R)-cystothiazoles 3], natural cystothiazole F 3 was found to be a 33:67 diastereomeric mixture [(4R,5S,6E,14S)-3:(4R,5S,6E,14R)-3 = 33:67]. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：513 / 519
页数：7
相关论文
共 50 条
  • [31] The first chemoenzymatic total synthesis of the phytotoxic nonenolide putaminoxin and its (5S,6E,9S)-diastereomer
    Dickmann, David
    Diekmann, Martin
    Holec, Claudia
    Pietruszka, Joerg
    TETRAHEDRON, 2019, 75 (06) : 689 - 696
  • [32] Enantioselective synthesis of the (5S, 6R, 9R) and (5S, 6R, 9S) analogs of lactacystin β-lactone
    Corey, EJ
    Li, WDZ
    TETRAHEDRON LETTERS, 1998, 39 (44) : 8043 - 8046
  • [33] Short practical synthesis of (3R,4R,5R,6R)-tetrahydroxyazepane and (3S,4S,5S,6S)-tetrahydroxyazepane from D- and L-chiro-inositol, respectively
    Painter, GF
    Falshaw, A
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (07): : 1157 - 1159
  • [34] (-)-(4R,5S)-4-methyl-3-[2(S)-phenoxypropionyl]-5-phenyloxazolidin-2-one
    Chavda, Sameer
    Eames, Jason
    Motevalli, Majid
    Malatesti, Nela
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O4043 - O4045
  • [35] Stereodivergent synthesis of (2S,3S,4R,5R)- and (2S,3S,4R,5S)-[3,4,5-D3]proline depending on the substituent of the γ-lactam ring
    Oba, M
    Miyakawa, A
    Nishiyama, K
    Terauchi, T
    Kainosho, M
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (25): : 9275 - 9278
  • [36] Synthesis of (3S,4R)-bengamide E
    Liu, Qi Jun
    Li, Hong
    Chen, Shao Peng
    Zhou, Guo Chun
    CHINESE CHEMICAL LETTERS, 2011, 22 (05) : 505 - 507
  • [37] Synthesis of (3S,4R)-bengamide E
    Qi Jun Liu~(a
    Chinese Chemical Letters, 2011, 22 (05) : 505 - 507
  • [38] (4S,5S,10S,13R,14R,17R)-8α,9α-epoxy-4α,14α-dimethyl-5α-cholestan-3-one
    Mazoir, N
    Giorgi, M
    Benharref, A
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2005, 61 : O3709 - O3711
  • [39] SYNTHESIS OF (2S,5S)-BISHYDROXYMETHYL-(3R,4R)-BISHYDROXYPYRROLIDINE FROM D-MANNITOL
    SHING, TKM
    TETRAHEDRON, 1988, 44 (23) : 7261 - 7264
  • [40] (3R,4R,5S)-5-ACETAMIDO-3,4-PIPERIDINEDIOL - A SELECTIVE HEXOSAMINIDASE INHIBITOR
    BERNOTAS, RC
    GANEM, B
    CARBOHYDRATE RESEARCH, 1987, 167 : 312 - 316
12345