Sulfanyl radical-induced cyclization of linalyl acetate to the iridane skeleton:: A short synthesis of (±)-dehydroiridomyrmecin

被引：11
|
作者：
Barrero, AF
Arseniyadis, S
Herrador, MM
del Moral, JFQ
Arteaga, JF
Sánchez, EM
机构：
[1] Univ Granada, Inst Biotechnol, Dept Organ Chem, E-18071 Granada, Spain
[2] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
来源：
SYNLETT | 2005年 / 04期
关键词：
sulfanyl radical; iridane skeleton; addition-cyclization reaction; polyprenes; dehydroiridomyrmecin;
D O I：
10.1055/s-2005-863729
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Sulfanyl radicals promote radical cyclization both in linalyl acetate (2) and its derivative 3, leading highly selectively to monoterpenoids with an iridane skeleton. We have investigated the addition of different sulfanyl radicals such as PhS center dot, 4-NO2C6H4S center dot and PhCH2CH2S center dot and found that the latter radical produces the best results (87-93%). Natural iridoid dehydroiridomyrmecin (1) at an overall yield of 28% was synthesized in four steps using this method.
引用
收藏
页码：591 / 594
页数：4
相关论文
共 50 条
  • [1] ORGANOSILICON RADICAL-INDUCED CYCLIZATION REACTIONS
    KRAUS, GA
    LIRAS, S
    [J]. TETRAHEDRON LETTERS, 1990, 31 (37) : 5265 - 5268
  • [2] Biosynthesis of Indole Diterpene Lolitrems: Radical-Induced Cyclization of an Epoxyalcohol Affording a Characteristic Lolitremane Skeleton
    Jiang, Yulu
    Ozaki, Taro
    Harada, Mei
    Miyasaka, Tadachika
    Sato, Hajime
    Miyamoto, Kazunori
    Kanazawa, Junichiro
    Liu, Chengwei
    Maruyama, Jun-ichi
    Adachi, Masaatsu
    Nakazaki, Atsuo
    Nishikawa, Toshio
    Uchiyama, Masanobu
    Minami, Atsushi
    Oikawa, Hideaki
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (41) : 17996 - 18002
  • [3] Mechanistic investigation on radical-induced construction of oxindoles: radical versus electrophilic cyclization
    Deng, Zhiqiang
    Jin, Lu
    Wu, Yong
    Zhao, Xiang
    [J]. RSC ADVANCES, 2017, 7 (49) : 30984 - 30989
  • [4] NEW SYNTHESIS OF LACTAMS AND SPIROLACTAMS RADICAL CYCLIZATION INDUCED BY MANGANESE(III) ACETATE
    COSSY, J
    LEBLANC, C
    [J]. TETRAHEDRON LETTERS, 1989, 30 (34) : 4531 - 4534
  • [5] STEREOSELECTIVE RADICAL-INDUCED CYCLIZATION OF UNSATURATED ALDONOLACTONES - SYNTHESIS OF HIGHLY FUNCTIONALIZED, ENANTIOMERICALLY PURE CYCLOPENTANE DERIVATIVES
    HORNEMAN, AM
    LUNDT, I
    SOTOFTE, I
    [J]. SYNLETT, 1995, (09) : 918 - &
  • [6] RADICAL CYCLIZATION OF BROMOMETHYLDIMETHYLSILYL PROPARGYL ETHERS - SYNTHESIS OF A CARBOCYCLIC CORE OF STEROID SKELETON BY A TANDEM RADICAL CYCLIZATION
    WU, SH
    JOURNET, M
    MALACRIA, M
    [J]. TETRAHEDRON LETTERS, 1994, 35 (46) : 8601 - 8604
  • [7] A TANDEM RADICAL CYCLIZATION APPROACH TO THE HEXAHYDROBENZOFURAN SKELETON FOR AVERMECTIN SYNTHESIS
    PARSONS, PJ
    WILLIS, PA
    EYLEY, SC
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (04) : 283 - 285
  • [8] A formal synthesis of (+)-α-allokainic acid via sulfanyl radical addition-cyclization reaction
    Miyata, O
    Ozawa, Y
    Ninomiya, T
    Aoe, K
    Hiramatsu, H
    Naito, T
    [J]. HETEROCYCLES, 1997, 46 : 321 - 333
  • [9] Radical cyclization in heterocycle synthesis. Part 10: A concise synthesis of (-)-kainic acid via sulfanyl radical addition-cyclization-elimination reaction
    Miyata, O
    Ozawa, Y
    Ninomiya, I
    Naito, T
    [J]. TETRAHEDRON, 2000, 56 (34) : 6199 - 6207
  • [10] RADICAL-INDUCED EPOXIDE FRAGMENTATION CHEMISTRY - ATOM TRANSFER CYCLIZATION OF IODOEPOXIDES TO CYCLOPENTANOLS
    RAWAL, VH
    IWASA, S
    [J]. TETRAHEDRON LETTERS, 1992, 33 (33) : 4687 - 4690
12345