The total synthesis of (±)-merrilactone A

被引：123
作者：
Birman, VB
Danishefsky, SJ
机构：
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
[2] Sloan Kettering Inst Canc Res, Bioorgan Chem Lab, New York, NY 10021 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 10期
关键词：
D O I：
10.1021/ja012495d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The total synthesis of the title compound has been accomplished in 20 steps. The key step is a free radical cyclization of vinyl bromide 29 to afford 30. The synthesis also features an efficient Diels-Alder reaction of 2,3-dimethylmaleic anhydride with 1-(tert-butyldimethylsiloxy)-butadiene. The oxetane moiety of merrilactone A is fashioned via a Payne-like rearrangement of a hydroxyepoxide (see 2 → 1). Copyright © 2002 American Chemical Society.
引用
收藏
页码：2080 / 2081
页数：2
相关论文
共 22 条
  • [1] A new synthetic route to β-unsubstituted β-lactones by intramolecular cyclization
    Alexandre, FR
    Legoupy, S
    Huet, F
    [J]. TETRAHEDRON, 2000, 56 (24) : 3921 - 3926
  • [2] Backman C, 1996, J NEUROSCI, V16, P5437
  • [3] STEREOSPECIFIC TOTAL SYNTHESIS OF GIBBERELLIC-ACID - KEY TRICYCLIC INTERMEDIATE
    COREY, EJ
    DANHEISER, RL
    CHANDRASEKARAN, S
    SIRET, P
    KECK, GE
    GRAS, JL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (25) : 8031 - 8034
  • [4] SIMPLE, EFFICIENT TOTAL SYNTHESIS OF CANTHARIDIN VIA A HIGH-PRESSURE DIELS-ALDER REACTION
    DAUBEN, WG
    KESSEL, CR
    TAKEMURA, KH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (22) : 6893 - 6894
  • [5] DEFOIN A, 1991, HELV CHIM ACTA, V74, P1665
  • [6] Functional recovery in parkinsonian monkeys treated with GDNF
    Gash, DM
    Zhang, ZM
    Ovadia, A
    Cass, WA
    Yi, A
    Simmerman, L
    Russell, D
    Martin, D
    Lapchak, PA
    Collins, F
    Hoffer, BJ
    Gerhardt, GA
    [J]. NATURE, 1996, 380 (6571) : 252 - 255
  • [7] Pharmacology of neurotrophic factors
    Hefti, F
    [J]. ANNUAL REVIEW OF PHARMACOLOGY AND TOXICOLOGY, 1997, 37 : 239 - 267
  • [8] HENBEST HB, 1956, CHEM IND-LONDON, P659
  • [9] Merrilactone A, a novel neurotrophic sesquiterpene dilactone from Illicium merrillianum
    Huang, JM
    Yokoyama, R
    Yang, CS
    Fukuyama, Y
    [J]. TETRAHEDRON LETTERS, 2000, 41 (32) : 6111 - 6114
  • [10] Structures of merrilactones B and C, novel anislactone-type sesquiterpenes from Illicium merrillianum, and chemical conversion of anislactone B to merrilactone A
    Huang, JM
    Yang, CS
    Tanaka, M
    Fukuyama, Y
    [J]. TETRAHEDRON, 2001, 57 (22) : 4691 - 4698
123