Investigating direct routes to an advanced intermediate for the synthesis of C-20 diterpene alkaloids

被引:17
|
作者
Williams, CM [1 ]
Mander, LN
Bernhardt, PV
Willis, AC
机构
[1] Univ Queensland, Sch Mol & Microbial Sci, St Lucia, Qld 4072, Australia
[2] Australian Natl Univ, Res Sch Chem, Canberra, ACT, Australia
关键词
diterpene alkaloids; silver (I); intramolecular Friedel-Crafts arylation; 3-azabicyclo[3.3.1]nonane;
D O I
10.1016/j.tet.2005.02.014
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rapid access to the ABCE ring system of the C-20 diterpene alkaloids was achieved by silver (I) promoted intramolecular Friedel-Crafts arylation of a functional group specific 5-bromo-3-azabicyclo[3.3.1]nonane derivative. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3759 / 3769
页数:11
相关论文
共 50 条
  • [41] STEROIDS AND SEX-HORMONES .244. SYNTHESIS OF C-20 EPIMERIC 7,8-DEHYDROBATRACHOTOXININ
    GRAF, W
    GOSSINGE.FE
    WEHRLI, H
    IMHOF, R
    HELVETICA CHIMICA ACTA, 1972, 55 (05) : 1545 - +
  • [42] Perhydroisoquinoline synthesis: C(20)-substituted analogs of yohimbine-type alkaloids
    Hart, DJ
    Ellis, DA
    HETEROCYCLES, 1998, 49 : 117 - 120
  • [43] SYNTHETIC STUDIES TOWARD COMPLEX DITERPENOIDS .9. NEW STEREOCONTROLLED SYNTHETIC ROUTE TO SOME INTERMEDIATES FOR DITERPENOID ALKALOIDS AND C-20 GIBBERELLINS
    GHATAK, UR
    CHAKRABARTY, S
    JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (07): : 1089 - 1094
  • [44] Structure, Synthesis, and Biological Activity of a C-20 Bisacetylenic Alcohol from a Marine Sponge Callyspongia sp.
    Shirouzu, Takayuki
    Watari, Kousuke
    Ono, Mayumi
    Koizumi, Keiichi
    Saiki, Ikuo
    Tanaka, Chiaki
    van Soest, Rob W. M.
    Miyamoto, Tomofumi
    JOURNAL OF NATURAL PRODUCTS, 2013, 76 (07): : 1337 - 1342
  • [45] The first enantioselective synthesis of cytotoxic marine natural product palau'imide and assignment of its C-20 stereochemistry
    Lan, Hong-Qiao
    Ruan, Yuan-Ping
    Huang, Pei-Qiang
    CHEMICAL COMMUNICATIONS, 2010, 46 (29) : 5319 - 5321
  • [46] DIRECT AND AUTOMATIC CAPILLARY GC ANALYSIS FOR MOLECULAR-WEIGHT DETERMINATION AND DISTRIBUTION IN CRUDE OILS AND CONDENSATES UP TO C-20
    DURAND, JP
    FAFET, A
    BARREAU, A
    HRC-JOURNAL OF HIGH RESOLUTION CHROMATOGRAPHY, 1989, 12 (04): : 230 - 233
  • [47] A Unifying Synthesis Approach to the C18-, C19-, and C20-Diterpenoid Alkaloids
    Kou, Kevin G. M.
    Kulyk, Svitlana
    Marth, Christopher J.
    Lee, Jack C.
    Doering, Nicolle A.
    Li, Beryl X.
    Gallego, Gary M.
    Lebold, Terry P.
    Sarpong, Richmond
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (39) : 13882 - 13896
  • [48] Efficient synthesis of the C/D rings of atisine-type C20-diterpenoid alkaloids
    De Lin Chen
    Feng Peng Wang
    Chinese Chemical Letters, 2012, 23 (12) : 1378 - 1380
  • [49] Efficient synthesis of the C/D rings of atisine-type C20-diterpenoid alkaloids
    Chen, De Lin
    Wang, Feng Peng
    CHINESE CHEMICAL LETTERS, 2012, 23 (12) : 1378 - 1380
  • [50] SYNTHESIS OF AN ALBERTA OIL SAND BITUMEN C-20 TRICYCLIC CARBOXYLIC-ACID BEARING A NOVEL DITERPENOID SKELETON
    KAUFMAN, TS
    GONZALEZSIERRA, M
    RUVEDA, EA
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (08): : 2323 - 2327