Enantioselective formal synthesis of tridemethylisovelleral

被引：6
|
作者：
Rome, Daniel [1 ]
Johansson, Martin [1 ]
Sterner, Olov [1 ]
机构：
[1] Lund Univ, Div Organ Chem, S-22100 Lund, Sweden
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 04期
关键词：
D O I：
10.1016/j.tetlet.2006.11.122
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and efficient synthetic route to the bicyclic alpha,beta-unsaturated beta-keto ester methyl (3aS,7aS)-6-oxo-2,3,3a,6,7,7ahexahydro-1H-indene-5-carboxylate, a versatile intermediate in the synthesis of biologically active unsaturated 1,4-dialdehydes, is described. The synthesis includes a chirality introducing nonenzymatic asymmetric desymmetrization (ADS) reaction of a cyclic nieso-anhydride 4 and a modified Hofmann method for preparing exocyclic dienes. The ester was synthesized in a moderate overall yield (19%) from 6 and with an excellent enantioselectivity (> 90%). (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：635 / 638
页数：4
相关论文
共 50 条
  • [41] An enantioselective formal synthesis of (+)-Gephyrotoxin 287C
    Miao, Lei
    Shu, Hong
    Noble, April R.
    Fournet, Steven P.
    Stevens, Edwin D.
    Trudell, Mark L.
    ARKIVOC, 2010, : 6 - 14
  • [42] Synergistic formal ring contraction for the enantioselective synthesis of spiropyrazolones
    Meazza, Marta
    Kamlar, Martin
    Jasikova, Lucie
    Formanek, Bedrich
    Mazzanti, Andrea
    Roithova, Jana
    Vesely, Jan
    Rios, Ramon
    CHEMICAL SCIENCE, 2018, 9 (30) : 6368 - 6373
  • [43] Highly enantioselective organocatalytic synthesis of piperidines. Formal synthesis of (-)-Paroxetine
    Valero, Guillem
    Schimer, Jiri
    Cisarova, Ivana
    Vesely, Jan
    Moyano, Albert
    Rios, Ramon
    TETRAHEDRON LETTERS, 2009, 50 (17) : 1943 - 1946
  • [44] Enantioselective Total Synthesis of (-)-Limaspermidine and Formal Synthesis of (-)-1-Acetylaspidoalbidine
    Zhang, Shao-Xiong
    Shen, Xiao-Lei
    Li, Ze-Qian
    Zou, Li-Wei
    Wang, Feng-Qun
    Zhang, Hong-Bin
    Shao, Zhi-Hui
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (22): : 11444 - 11449
  • [45] Formal syntheses of (−)-isoretronecanol, (+)-laburnine, and a concise enantioselective synthesis of (+)-turneforcidine
    Yu-Fu Liang
    Chuang-Chung Chung
    Meng-Wen Huang
    Biing-Jiun Uang
    The Journal of Antibiotics, 2019, 72 : 397 - 406
  • [46] Enantioselective Synthesis of α-Stereogenic γ-Keto Esters via Formal Umpolung
    Prakash, G. K. Surya
    Wang, Fang
    Zhang, Zhe
    Ni, Chuanfa
    Haiges, Ralf
    Olah, George A.
    ORGANIC LETTERS, 2012, 14 (13) : 3260 - 3263
  • [47] Enantioselective, Organocatalytic Strategy for the Oxazolomycin Core: Formal Synthesis of (+)-Neooxazolomycin
    Chaheine, Christian M.
    Gladen, Paul T.
    Abbasov, Mikail E.
    Romo, Daniel
    ORGANIC LETTERS, 2020, 22 (23) : 9282 - 9286
  • [48] A formal enantioselective synthesis of (+)-dodoneine via cyclic sulfate methodology
    Vuppalapati, Srinivasu V. N.
    Putapatri, Siddamal R.
    Kantevari, Srinivas
    ARKIVOC, 2009, : 217 - 226
  • [49] Enantioselective formal total synthesis of the antitumor macrolide bryostatin 7
    Manaviazar, Soraya
    Frigerio, Mark
    Bhatia, Gurpreet S.
    Hummersone, Marc G.
    Aliev, Abil E.
    Hale, Karl J.
    ORGANIC LETTERS, 2006, 8 (20) : 4477 - 4480
  • [50] A formal synthesis of (-)-paroxetine by enantioselective ring enlargement of a trisubstituted prolinol
    Cossy, J
    Mirguet, O
    Pardo, DG
    Desmurs, JR
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (21) : 3543 - 3551
12345