Formal total synthesis of (+)-didemniserinolipid B

被引:14
|
作者
Prasad, Kavirayani R. [1 ]
Gandi, Vasudeva Rao [1 ]
机构
[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India
关键词
STEREOSELECTIVE TOTAL-SYNTHESIS; ACID;
D O I
10.1016/j.tetasy.2010.11.006
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The formal total synthesis of (+)-didemniserinolipid B, a marine tunicate possessing a 6,8-dioxabicyclo[3.2.1]octane framework, was accomplished starting from L-(+)-tartaric acid. The key transformations in the synthesis include the elaboration of a gamma-hydroxy-amide readily obtained by desymmetrization of tartaric acid bis-amide via the controlled addition of a Grignard reagent followed by stereoselective reduction of the resulting ketone. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2848 / 2852
页数:5
相关论文
共 50 条
  • [31] Total synthesis of Xestodecalactone A and formal total synthesis of Sporostatin
    De Joarder, Dripta
    Jennings, Michael
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [32] Preparation of 3-alkylpyridines. Formal total synthesis of Haliclamines A and B
    Baldwin, JE
    James, DA
    Lee, V
    TETRAHEDRON LETTERS, 2000, 41 (05) : 733 - 736
  • [33] Enantiocontrolled formal total synthesis of paeonilactone A and B from (S)-(+)-carvone
    Ronn, M
    Andersson, PG
    Backvall, JE
    ACTA CHEMICA SCANDINAVICA, 1998, 52 (05): : 524 - 527
  • [34] Formal Total Synthesis of Lactimidomycin
    Nagasawa, Tomohiro
    Kuwahara, Shigefumi
    ORGANIC LETTERS, 2013, 15 (12) : 3002 - 3005
  • [35] Formal total synthesis of (+)-methynolide
    Cossy, J
    Bauer, D
    Bellosta, V
    TETRAHEDRON, 2002, 58 (29) : 5909 - 5922
  • [36] A formal total synthesis of the salicylihalamides
    Herb, C
    Maier, ME
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (21): : 8129 - 8135
  • [37] FORMAL TOTAL SYNTHESIS OF (-)-INDOLMYCIN
    AKITA, H
    KAWAGUCHI, T
    ENOKI, Y
    OISHI, T
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (02) : 323 - 328
  • [38] A FORMAL TOTAL SYNTHESIS OF (+/-)-FRULLANOLIDE
    BANERJEE, AK
    CANUDASGONZALEZ, N
    HERNANDEZ, SB
    FUENTES, SP
    PENAMATHEUD, CA
    JOURNAL OF CHEMICAL RESEARCH-S, 1990, (05): : 158 - 159
  • [39] A FORMAL TOTAL SYNTHESIS OF APLYSIATOXIN
    OKAMURA, H
    KURODA, S
    IKEGAMI, S
    ITO, Y
    KATSUKI, T
    YAMAGUCHI, M
    TETRAHEDRON LETTERS, 1991, 32 (38) : 5141 - 5142
  • [40] A formal total synthesis of (-)-limaspermine
    Fukuda, Y
    Shindo, M
    Shishido, K
    HETEROCYCLES, 2004, 62 : 787 - 792