Bronsted acid-mediated annulations of pyrroles featuring N-tethered α,β-unsaturated ketones and esters: Total syntheses of (±)-tashiromine and (±)-indolizidine 209I

被引：10
作者：
Olivier, Wesley J. [1 ]
Gardiner, Michael G. [1 ]
Bissember, Alex C. [1 ]
Smith, Jason A. [1 ]
机构：
[1] Univ Tasmania, Sch Nat Sci Chem, Hobart, Tas 7001, Australia
来源：
TETRAHEDRON | 2018年 / 74卷 / 38期
关键词：
Pyrrole; Bronsted acid; Intramolecular Michael addition; Total synthesis; Indolizidine; Tashiromine; INDOLIZIDINE; ALKALOIDS; QUINOLIZIDINES; PYRROLIZIDINE; RESOLUTION; OXIDATION; ROUTE; 167B;
D O I：
10.1016/j.tet.2018.04.067
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
This study provides the first report of the construction of tetrahydroindolizines and tetrahydropyrrolo [1,2-a]azepines via Bronsted acid-mediated annulation of pyrroles featuring N-tethered alpha,beta-unsaturated esters. In addition, the Bronsted acid-catalyzed cyclization of pyrroles featuring pendant alpha,beta-unsaturated ketones was applied to complete total syntheses of the indolizidine alkaloids (+/-)-tashiromine and (+/-)-indolizidine 209I. (C) 2018 Published by Elsevier Ltd.
引用
收藏
页码：5436 / 5441
页数：6
相关论文
共 37 条
  • [1] ABRAHAM DJ, 1972, TETRAHEDRON LETT, P909, DOI 10.1016/S0040-4039(01)84471-3
  • [2] FORMATION OF CARBON-CARBON BONDS VIA QUINONE METHIDE-INITIATED CYCLIZATION REACTIONS
    ANGLE, SR
    ARNAIZ, DO
    BOYCE, JP
    FRUTOS, RP
    LOUIE, MS
    MATTSONARNAIZ, HL
    RAINIER, JD
    TURNBULL, KD
    YANG, WJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) : 6322 - 6337
  • [3] PARA-QUINONE METHIDE INITIATED INTRAMOLECULAR ELECTROPHILIC SUBSTITUTION-REACTIONS
    ANGLE, SR
    LOUIE, MS
    MATTSON, HL
    YANG, WJ
    [J]. TETRAHEDRON LETTERS, 1989, 30 (10) : 1193 - 1196
  • [4] Convergent synthesis and preliminary biological evaluation of (±)-B-norrhazinal
    Banwell, M
    Edwards, A
    Smith, J
    Hamel, E
    Verdier-Pinard, P
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (10): : 1497 - 1499
  • [5] The influence of chiral auxiliaries and catalysts on the selectivity of intramolecular conjugate additions of pyrrole to N-tethered Michael acceptors
    Banwell, MG
    Beck, DAS
    Smith, JA
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (02) : 157 - 159
  • [6] Exploiting multiple nucleophilic sites on pyrrole for the assembly of polyheterocyclic frameworks:: application to a formal total synthesis of (±)-aspidospermidine
    Banwell, MG
    Smith, JA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (23): : 2613 - 2618
  • [7] A SIMPLE ROUTE TO THE INDOLIZIDINE ALKALOID SKELETON
    BARTON, DHR
    PEREIRA, MMMA
    TAYLOR, DK
    [J]. TETRAHEDRON LETTERS, 1994, 35 (49) : 9157 - 9158
  • [8] Synthesis of the Stenine Ring System from Pyrrole
    Bates, Roderick W.
    Sridhar, S.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (12) : 5026 - 5035
  • [9] Beck DAS, 2006, THESIS
  • [10] Bergman J., 2011, 5 MEMBERED HETEROCYC, P4
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