Synthesis of harzialactone A and its isomers from D-glucose and assignment of absolute stereochemistry

被引：21
|
作者：
Mereyala, HB [1 ]
Joe, M [1 ]
Gadikota, RR [1 ]
机构：
[1] Indian Inst Chem Technol, Div Organ Chem 3, Hyderabad 500007, Andhra Pradesh, India
来源：
TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 20期
关键词：
D O I：
10.1016/S0957-4166(00)00389-X
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The synthesis of the marine metabolite (3R,5R)-harzialactone A 1 from D-glucose is described. Syntheses of all the isomers (3S,5R)-2, (3R,5S)-3 and (3S,5S)-4 of 1 are also described and the absolute stereochemistry for the natural product 1 is assigned unambiguously. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：4071 / 4081
页数：11
相关论文
共 50 条
  • [31] Total synthesis of paniculide A from D-glucose
    Amano, S
    Takemura, N
    Ohtsuka, M
    Ogawa, S
    Chida, N
    TETRAHEDRON, 1999, 55 (13) : 3855 - 3870
  • [32] SYNTHESIS OF INSECT PHEROMONES FROM D-GLUCOSE
    SUM, PE
    WEILER, L
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1979, (SEP): : 37 - 37
  • [33] TOTAL SYNTHESIS OF (+)-LACTACYSTIN FROM D-GLUCOSE
    CHIDA, N
    TAKEOKA, J
    TSUTSUMI, N
    OGAWA, S
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (07) : 793 - 794
  • [34] STEREOSELECTIVE SYNTHESIS OF (+)-CERULENIN FROM D-GLUCOSE
    SUEDA, N
    OHRUI, H
    KUZUHARA, H
    TETRAHEDRON LETTERS, 1979, (22) : 2039 - 2042
  • [35] SYNTHESIS OF (-)-BACTOBOLIN FROM D-GLUCOSE AND FROM (+)-ACTINOBOLIN
    WARD, DE
    GAI, YZ
    KALLER, BF
    TETRAHEDRON LETTERS, 1994, 35 (21) : 3485 - 3488
  • [36] TOTAL SYNTHESIS OF (+)-LYCORICIDINE AND ITS 2-EPIMER FROM D-GLUCOSE
    CHIDA, N
    OHTSUKA, M
    OGAWA, S
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16): : 4441 - 4447
  • [37] L-GLUCOSE - A CONVENIENT SYNTHESIS FROM D-GLUCOSE
    SZAREK, WA
    HAY, GW
    VYAS, DM
    ISON, ER
    HRONOWSKI, LJJ
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (04): : 671 - 674
  • [38] SYNTHESIS OF D-ERYTHROASCORBIC ACID FROM D-GLUCOSE
    GAN, LX
    SEIB, PA
    CARBOHYDRATE RESEARCH, 1991, 220 : 117 - 125
  • [39] Stereocontrolled synthesis of the aconitine D ring from D-glucose
    Pocock, Ian A.
    Doulcet, Julien
    Rice, Craig R.
    Sweeney, Joseph B.
    Gill, Duncan M.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (21) : 4347 - 4352
  • [40] STEREOSELECTIVE SYNTHESIS OF (+)-TETRAHYDROCERULENIN AND (-)-TETRAHYDROCERULENIN FROM D-GLUCOSE CORRECT ABSOLUTE-CONFIGURATION OF NATURAL CERULENIN
    OHRUI, H
    EMOTO, S
    TETRAHEDRON LETTERS, 1978, (24) : 2095 - 2098
12345