Total Synthesis of the Neoclerodane Diterpene Salvinorin A via an Intramolecular Diels-Alder Strategy

被引：12
|
作者：
Wang, Yuzhou [1 ]
Metz, Peter [1 ]
机构：
[1] Tech Univ Dresden, Fak Chem & Lebensmittelchem, Organ Chem I, Bergstr 66, D-01069 Dresden, Germany
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 11期
关键词：
KAPPA-OPIOID RECEPTOR; SALVIA-DIVINORUM; AGONIST; PRODUCTS; REAGENT; MICE;
D O I：
10.1021/acs.orglett.8b01357
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A concise total synthesis of the neoclerodane diterpene salvinorin A from 3-furaldehyde is reported using two highly diastereoselective intramolecular Diels-Alder reactions (IMDA) as the key transformations.
引用
收藏
页码：3418 / 3421
页数：4
相关论文
共 50 条
  • [31] Total synthesis of eustifolines A-D and glycomaurrol via a divergent Diels-Alder strategy
    Lebold, Terry P.
    Kerr, Michael A.
    ORGANIC LETTERS, 2007, 9 (10) : 1883 - 1886
  • [32] Synthesis of the decalin core of codinaeopsin via an intramolecular Diels-Alder reaction
    Ramanathan, Mani
    Tan, Chun-Jui
    Chang, Wen-Jung
    Tsai, Hui-Hsu Gavin
    Hou, Duen-Ren
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (23) : 3846 - 3854
  • [33] Taxane synthesis: The intramolecular Diels-Alder approach
    Winkler, JD
    Bhattacharya, SK
    Liotta, F
    Batey, RA
    Kim, HS
    Saraiva, M
    Chandramouli, SV
    Kelly, RC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 211 : 47 - ORGN
  • [34] SYNTHESIS OF INDOLIZIDINE ALKALOIDS VIA THE INTRAMOLECULAR IMINO DIELS-ALDER REACTION
    KHATRI, NA
    SCHMITTHENNER, HF
    SHRINGARPURE, J
    WEINREB, SM
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (21) : 6387 - 6393
  • [35] CYTOCHALASAN SYNTHESIS - MACROCYCLE FORMATION VIA INTRAMOLECULAR DIELS-ALDER REACTIONS
    THOMAS, EJ
    ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (08) : 229 - 235
  • [36] Synthesis of the tricyclic core of vinigrol via an intramolecular Diels-Alder reaction
    Grise, Christiane M.
    Tessier, Guillaume
    Barriault, Louis
    ORGANIC LETTERS, 2007, 9 (08) : 1545 - 1548
  • [37] Total synthesis of (+)-cassaine via transannular diels-alder reaction
    Phoenix, Serge
    Reddy, Maddi Sridhar
    Deslongchamps, Pierre
    Journal of the American Chemical Society, 2008, 130 (42): : 13989 - 13995
  • [38] Total synthesis of (+)-gelsemine via an organocatalytic Diels-Alder approach
    Chen, Xiaoming
    Duan, Shengguo
    Tao, Cheng
    Zhai, Hongbin
    Qiu, Fayang G.
    NATURE COMMUNICATIONS, 2015, 6
  • [39] Total synthesis of (+)-cassaine via transannular Diels-Alder reaction
    Phoenix, Serge
    Reddy, Maddi Sridhar
    Deslongchamps, Pierre
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (42) : 13989 - 13995
  • [40] The Diels-Alder reaction in total synthesis
    Nicolaou, KC
    Snyder, SA
    Montagnon, T
    Vassilikogiannakis, G
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (10) : 1668 - 1698
12345