Synthesis of a 14 beta-hydroxysteroid using the transannular Diels-Alder strategy

被引:0
|
作者
Ouellet, L [1 ]
Langlois, P [1 ]
Deslongchamps, P [1 ]
机构
[1] UNIV SHERBROOKE,FAC SCI,DEPT CHIM,ORGAN SYNTH LAB,SHERBROOKE,PQ J1K 2R1,CANADA
关键词
cardenolides; cardiac glycosides; 14; beta-hydroxysteroid; transannular Diels-Alder reaction; macrocyclisation;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Macrocyclic TCC triene 1, generated by an intramolecular alkylation of a beta-ketoester on a pi-allylpalladium complex followed by dehydrogenation, underwent a highly stereoselective transannular Diels-Alder reaction affording the tetracyclic compound 2 in an excellent yield.
引用
收藏
页码:689 / 690
页数:2
相关论文
共 50 条
  • [41] A Diels-Alder strategy towards a benzonaphthopyranoquinone
    Tapia, RA
    Alegría, L
    Valderrama, JA
    Cortés, M
    Pautet, F
    Fillion, H
    TETRAHEDRON LETTERS, 2001, 42 (05) : 887 - 889
  • [42] Transannular Hetero Diels-Alder Reaction of Macrocyclic a, QQ -Unsaturated Thioketones and Synthesis of Oxonin Derivatives by Desulfurization of the Transannular Adducts
    Moriyama, S.
    Karakasa, T.
    Inoue, T.
    Kurashima, K.
    Synlett, (01):
  • [43] STEREOCONTROLLED CHIRAL SYNTHESIS OF A TRANS-ANTI-TRANS TRICYCLE BY A TRANSANNULAR DIELS-ALDER REACTION
    MARINIER, A
    DESLONGCHAMPS, P
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1992, 70 (09): : 2350 - 2364
  • [44] A Diels-Alder/Retro diels-alder strategy to synthesize polymers bearing maleimide side chains
    Dispinar, Tugba
    Sanyal, Rana
    Sanyal, Amitav
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2007, 45 (20) : 4545 - 4551
  • [45] FIRST TRANSANNULAR DIELS-ALDER REACTIONS INVOLVING TETRASUBSTITUTED NONACTIVATED DIENOPHILES
    ROBERGE, JY
    GIGUERE, P
    SOUCY, P
    DORY, YL
    DESLONGCHAMPS, P
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (08): : 1820 - 1829
  • [46] Synthesis of norbornene derivative using Diels-Alder reaction
    Park, Jun-Seong
    Oh, Hyun-Chul
    Park, Yong-Sung
    Woo, Je-Wan
    ADVANCED DESIGN TECHNOLOGY, 2012, 421 : 136 - +
  • [47] Synthesis of amlodipine using aza Diels-Alder reaction
    Kim, SC
    Choi, KM
    Cheong, CS
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2002, 23 (01) : 143 - 144
  • [48] Chiral anthracenes as a Diels-Alder/retro Diels-Alder template in asymmetric synthesis.
    Sanyal, A
    Snyder, JK
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 220 : U121 - U121
  • [49] Transannular Diels-Alder cyclization of substituted 13-membered trienes. An approach to the BCD[6.6.5] rings of the 14 beta-hydroxysteroids
    Langlois, P
    Soucy, P
    Dory, YL
    Deslongchamps, P
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1996, 74 (02): : 129 - 143
  • [50] A DIRECT TOTAL SYNTHESIS OF (+)-LONGIFOLENE VIA AN INTRAMOLECULAR DIELS-ALDER STRATEGY
    LEI, B
    FALLIS, AG
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) : 4609 - 4610