A stereocontrolled total synthesis of (±)-norzizanone

被引：13
|
作者：
Pati, LC [1 ]
Roy, A [1 ]
Mukherjee, D [1 ]
机构：
[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Calcutta 700032, W Bengal, India
来源：
TETRAHEDRON LETTERS | 2000年 / 41卷 / 52期
关键词：
terpenes; cyclisation; desulfurisation; hydroxylation; rearrangement;
D O I：
10.1016/S0040-4039(00)01861-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A stereocontrolled total synthesis of (+/-)-norzizanone 1 has been efficiently accomplished involving base-induced rearrangement of the mesylate 17 as the key step. Aryl participated intramolecular cyclisation of the bromophenol 11 provided the tricyclic dienone 12. which was stereoselectively converted into the mesylate 17. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：10353 / 10356
页数：4
相关论文
共 50 条
  • [31] Stereocontrolled Total Synthesis of PolygalolideA
    Yamada, Hitomi
    Adachi, Masaatsu
    Isobe, Minoru
    Nishikawa, Toshio
    CHEMISTRY-AN ASIAN JOURNAL, 2013, 8 (07) : 1428 - 1435
  • [32] A STEREOCONTROLLED TOTAL SYNTHESIS OF HOBARTINE
    BARDEN, TC
    GRIBBLE, GW
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1985, 190 (SEP): : 34 - ORN
  • [33] STEREOCONTROLLED TOTAL SYNTHESIS OF (+/-)-MAYTANSINOL
    ISOBE, M
    KITAMURA, M
    GOTO, T
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (18) : 4997 - 4999
  • [34] A stereocontrolled total synthesis of (±)-zizaene
    Pati, LC
    Roy, A
    Mukherjee, D
    TETRAHEDRON, 2002, 58 (09) : 1773 - 1778
  • [35] Stereocontrolled Total Synthesis of Nonenolide
    Sudina, Purushotham Reddy
    Motati, Damoder Reddy
    Seema, Aravind
    JOURNAL OF NATURAL PRODUCTS, 2018, 81 (06): : 1399 - 1404
  • [36] STEREOCONTROLLED TOTAL SYNTHESIS OF LIPOXINS-A
    NICOLAOU, KC
    VEALE, CA
    WEBBER, SE
    KATERINOPOULOS, H
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (25) : 7515 - 7518
  • [37] Stereocontrolled total synthesis of (+)-paraherquamide B
    J Am Chem Soc, 3 (557):
  • [38] Stereocontrolled total synthesis of (-)-ephedradine A (orantine)
    Kurosawa, W
    Kan, T
    Fukuyama, T
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (27) : 8112 - 8113
  • [39] Stereocontrolled total synthesis of (-)-kainic acid
    Sakaguchi, Hiroshi
    Tokuyama, Hidetoshi
    Fukuyama, Tohru
    ORGANIC LETTERS, 2007, 9 (09) : 1635 - 1638
  • [40] Stereocontrolled total synthesis of (±)-pisiferol and (±)-pisiferal
    Pati, LC
    Mukherjee, D
    TETRAHEDRON LETTERS, 2004, 45 (51) : 9451 - 9453
12345