Studies Towards the Synthesis of Crotogoudin

被引：11
作者：
Ushakov, Dmitry B. [1 ]
Maier, Martin E. [1 ]
机构：
[1] Univ Tubingen, Inst Organ Chem, D-72076 Tubingen, Germany
来源：
SYNLETT | 2013年 / 24卷 / 06期
关键词：
crotogoudin; atisane; diterpene; domino Michael reaction; Stork reductive alkylation; ENANTIOSELECTIVE TOTAL-SYNTHESIS; STEREOSELECTIVE TOTAL-SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; REDUCTIVE ALKYLATION; MICHAEL REACTION; ACID; ATIS-16-EN-19-OATE; TRACHYLOBANE; DITERPENOIDS; COMBINATION;
D O I：
10.1055/s-0032-1318366
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An effective synthesis of the tricyclic core structure of the new diterpene crotogoudin was achieved. The synthesis features an intermolecular domino Michael reaction to construct a bicyclo[2.2.2] octane motif and an aldol condensation to close ring B. Stork reductive alkylation with allyl bromide proceeded from the beta side, resulting in the wrong stereochemistry at C-10.
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收藏
页码：705 / 708
页数：4
相关论文
共 59 条
  • [1] A unified synthetic approach to trachylobane-, beyerane-, atisane- and kaurane-type diterpenes
    Abad, A
    Agulló, C
    Cuñat, AC
    Marzal, ID
    Navarto, I
    Gris, A
    [J]. TETRAHEDRON, 2006, 62 (14) : 3266 - 3283
  • [2] Abad A, 2001, SYNLETT, P349
  • [3] Diastereoselective synthesis of antiquorin and related polyoxygenated atisene-type diterpenes
    Abad, Antonio
    Agullo, Consuelo
    Cunat, Ana C.
    Marzal, Ignacio de Alfonso
    Gris, Antonio
    Navarro, Ismael
    de Arellano, Carmen Ramirez
    [J]. TETRAHEDRON, 2007, 63 (07) : 1664 - 1679
  • [4] [Anonymous], 1993, ANGEW CHEM
  • [5] Arndt F, 1935, ORG SYNTH, V15, P3
  • [6] Arndt F., 1943, Org. Synth, V2, P165
  • [7] INTRAMOLECULAR PHOTOADDITION OF TERMINAL ALLENES TO CONJUGATED CYCLOHEXENONES
    BECKER, D
    HAREL, Z
    NAGLER, M
    GILLON, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (17) : 3297 - 3306
  • [8] Dye-sensitized photooxygenation of sugar-furans as synthetic strategy for novel C-nucleosides and functionalized exo-glycals
    Cermola, Flavio
    Iesce, M. Rosaria
    [J]. TETRAHEDRON, 2006, 62 (46) : 10694 - 10699
  • [9] CYCLOALCOYLATION .1. NOUVEAU MODE DE SYNTHESE DES DECALONES .1.
    CONIA, JM
    ROUESSAC, F
    [J]. TETRAHEDRON, 1961, 16 (1-4) : 45 - &
  • [10] de Boer T.J., 1963, ORG SYNTH, V4, P250
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