Towards a total synthesis of ustiloxins A & B. Stereocontrolled synthesis of (2S,4S,6S)-4-hydroxy-5-phenylsulfinylnorvaline

被引：40
|
作者：
Hutton, CA
White, JM
机构：
[1] School of Chemistry, University of Melbourne, Parkville
来源：
TETRAHEDRON LETTERS | 1997年 / 38卷 / 09期
关键词：
D O I：
10.1016/S0040-4039(97)00110-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A short, stereocontrolled synthesis of (2S,4S,6S)-4-hydroxy-5-phenylsulfinylnorvaline (8), an unusual amino acid component of ustiloxins A & B, has been achieved. Stereoselective bromolactonisation of N-Boc-(S)-allylglycine (3) is followed by substitution of the bromide 4a with thiophenol to give the corresponding sulfide 5. Highly stereoselective oxidation of the sulfide 5 gives the corresponding sulfoxide 6a. Removal of the Boc group and lactone ring opening then complete the synthesis of the unusual amino acid. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码：1643 / 1646
页数：4
相关论文
共 50 条
  • [41] Synthesis of (+)-(S)-streptenol A and biomimetic synthesis of (2R,4S)- and (2S,4S)-2-(pent-3-enyl)piperidin-4-ol
    Dollt, H
    Hammann, P
    Blechert, S
    HELVETICA CHIMICA ACTA, 1999, 82 (07) : 1111 - 1121
  • [42] SYNTHESIS OF (+)-(2S,6S)-TRANS-ALPHA-IRONE AND OF (-)-(2S,6S)-TRANS-GAMMA-IRONE
    HELMLINGER, D
    FRATER, G
    HELVETICA CHIMICA ACTA, 1989, 72 (07) : 1515 - 1521
  • [43] Synthesis of (2S,3R,4S),(2S,3S,4R)-epoxyprolines and aminohydroxyprolines
    Robinson, JK
    Lee, V
    Claridge, TDW
    Baldwin, JE
    Schofield, CJ
    TETRAHEDRON, 1998, 54 (5-6) : 981 - 996
  • [44] Total Synthesis of Hemerocallisamine I Paved by Gram-Scale Synthesis of (2S,4S)-4-Hydroxyglutamic Acid Lactone
    Pincekova, Lucia
    Janciova, Eva
    Berkes, Dusan
    Gyepes, Robert
    Kolarovic, Andrej
    Caletkova, Ol'ga
    MOLECULES, 2023, 28 (05):
  • [45] A PRACTICAL STEREOSELECTIVE SYNTHESIS OF (2S,4S)4-TERT-BUTOXYCARBONYLAMINO-2-METHYLPYRROLIDINE
    LI, Q
    CHU, DTW
    RAYE, K
    CLAIBORNE, A
    SEIF, L
    MACRI, B
    PLATTNER, JJ
    TETRAHEDRON LETTERS, 1995, 36 (46) : 8391 - 8394
  • [46] PERISELECTIVE REACTIONS OF TROPONE - A NOVEL TANDEM PI(6S)+PI(4S), PI(4S)+PI(2S) REACTION WITH CYCLOHEPTATRIENE AND PI(4S)+PI(2S) CYCLOADDITION WITH CYCLOHEXA-2,4-DIENONE
    SINGH, V
    SHARMA, U
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1995, 34 (10): : 847 - 850
  • [47] AN EFFICIENT SYNTHESIS OF (2S,4S)-2-SUBSTITUTED 4-MERCAPTOPYRROLIDINE DERIVATIVES
    MATSUMURA, H
    BANDO, T
    SUNAGAWA, M
    HETEROCYCLES, 1995, 41 (01) : 147 - 159
  • [48] Synthesis of (6S)-6-hydroxy-4-epi-shikimic acid
    Griesbeck, Axel G.
    Miara, Claus
    Neudoerfl, Joerg
    ARKIVOC, 2007, : 216 - 223
  • [49] A study of polychlorinated leucine derivatives:: synthesis of (2S,4S)-5,5-dichloroleucine
    Ardá, A
    Jiménez, C
    Rodríguez, J
    TETRAHEDRON LETTERS, 2004, 45 (16) : 3241 - 3243
  • [50] Combinatorial solution-phase synthesis of (2S,4S)-4-acylamino-5-oxopyrrolidine-2-carboxamides
    Malavasic, Crt
    Brulc, Blaz
    Cebasek, Petra
    Dahmann, Georg
    Heine, Niklas
    Bevk, David
    Groselj, Uros
    Meden, Anton
    Stanovnik, Branko
    Svete, Jurij
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2007, 9 (02): : 219 - 229
12345