Application of an organozinc reagent derived from (S)-pyroglutamic acid:: a formal synthesis of epibatidine

被引：28
|
作者：
Karstens, WFJ [1 ]
Moolenaar, MJ [1 ]
Rutjes, FPJT [1 ]
Grabowska, U [1 ]
Speckamp, WN [1 ]
Hiemstra, H [1 ]
机构：
[1] Univ Amsterdam, Inst Mol Chem, Organ Chem Lab, NL-1018 WS Amsterdam, Netherlands
来源：
TETRAHEDRON LETTERS | 1999年 / 40卷 / 49期
关键词：
epibatidine; organozinc reagent; N-acyliminium ions; azabicylo[2.2.1]heptanes;
D O I：
10.1016/S0040-4039(99)01808-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A formal total synthesis of natural (-)-epibatidine has been developed. Key steps in the synthesis are a copper(I)-mediated coupling of an (S)-pyroglutamic acid-derived organozine reagent with 1-iodo-3-trimethylsilyl-1-propyne and an N-acyl- or N-sulfonyliminium ion cyclization, Following this route, various N-protected hydroxylactams were converted into 7-azabicylo[2,2,1]heptane derivatives, (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：8629 / 8632
页数：4
相关论文
共 50 条
  • [1] Functionalised pyrrolidinones derived from (S)-pyroglutamic acid
    Beard, MJ
    Bailey, JH
    Cherry, DT
    Moloney, MG
    Shim, SB
    Statham, KA
    Bamford, MJ
    Lamont, RB
    TETRAHEDRON, 1996, 52 (10) : 3719 - 3740
  • [2] Practical synthesis of (S)-pyroglutamic acid
    Barretto, Fernando Alves
    Cunha, Silvio
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2024, 61 (06) : 955 - 957
  • [3] CARBONYLATIVE COUPLING OF AN AMINO ACID-DERIVED ORGANOZINC REAGENT WITH FUNCTIONALIZED ARYL IODIDES - SYNTHESIS OF KYNURENINE
    JACKSON, RFW
    TURNER, D
    BLOCK, MH
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (21) : 2207 - 2208
  • [4] Functionalised Pyrrolidinones Derived from (S)-Pyroglutamic Acid by Cycloaddition Reactions
    Tetrahedron, 34 (11731):
  • [5] Functionalised pyrrolidinones derived from (S)-pyroglutamic acid by cycloaddition reactions
    Bailey, JH
    Cherry, DT
    Crapnell, KM
    Moloney, MG
    Shim, SB
    Bamford, MJ
    Lamont, RB
    TETRAHEDRON, 1997, 53 (34) : 11731 - 11744
  • [6] SYNTHESIS OF (+)-1-DEOXYNOJIRIMYCIN FROM (S)-PYROGLUTAMIC ACID
    IKOTA, N
    HETEROCYCLES, 1989, 29 (08) : 1469 - 1472
  • [7] α-chloronitroso compounds derived from carbohydrate ketones:: cycloadditions with cyclic dienes, a synthesis of (-)-physoperuvine and a formal synthesis of (+)-epibatidine
    Hall, A
    Bailey, PD
    Rees, DC
    Rosair, GM
    Wightman, RH
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (03): : 329 - 343
  • [8] Stereoselective synthesis of alexine stereoisomers from (S)-pyroglutamic acid
    Ikota, N
    Nakagawa, H
    Ohno, S
    Noguchi, K
    Okuyama, K
    TETRAHEDRON, 1998, 54 (31) : 8985 - 8998
  • [9] Spirocyclic systems derived from pyroglutamic acid
    Cowley, Andrew R.
    Hill, Thomas J.
    Kocis, Petr
    Moloney, Mark G.
    Stevenson, Robert D.
    Thompson, Amber L.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (20) : 7042 - 7056
  • [10] α-Chloronitroso compounds derived from carbohydrate ketones: Cycloadditions with cyclic dienes, a synthesis of (-)-physoperuvine and a formal synthesis of (+)-epibatidine
    Hall, Adrian
    Bailey, Patrick D.
    Rees, David C.
    Rosair, Georgina M.
    Wightman, Richard H.
    Journal of the Chemical Society, Perkin Transactions 1, 2000, (03): : 329 - 343
12345