Facile enantiodivergent approach to 5-hydroxy-5,6-dihydro-2(1H)-pyridones.: First total synthesis of both enantiomers of pipermethystine

被引：33
作者：
Arrayás, RG [1 ]
Alcudia, A [1 ]
Liebeskind, LS [1 ]
机构：
[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA
来源：
ORGANIC LETTERS | 2001年 / 3卷 / 21期
关键词：
D O I：
10.1021/ol010183+
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] A novel enantiodivergent approach to 5-hydroxy-5,6-dihydro-2(lh)-pyridones using a ring closing metathesis and a lipase-mediated kinetic resolution as key steps is described and applied to the first synthesis of both enantiomers of pipermethystine.
引用
收藏
页码：3381 / 3383
页数：3
相关论文
共 43 条
  • [1] STEREOCONTROLLED SYNTHESIS OF 1,5-DIDEOXY-1,5-IMINO-ALLITOL (1-DEOXY-ALLONOJIRIMYCIN) FROM SERINE
    ALTENBACH, HJ
    HIMMELDIRK, K
    [J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (05) : 1077 - 1080
  • [2] [Anonymous], 1985, ALKALOIDS CHEM BIOL
  • [3] Arisawa M, 1997, SYNLETT, P1179
  • [4] Balasubramanian M., 1996, COMPREHENSIVE HETERO, V5, P245, DOI 10.1016/B978-008096518-5.00109
  • [5] An efficient and facile three-step synthesis of 5-amino-5-deoxy-D-pentonolactams from unprotected D-pentono-1,4-lactones.
    Bouchez, V
    Stasik, I
    Beaupere, D
    Uzan, R
    [J]. TETRAHEDRON LETTERS, 1997, 38 (44) : 7733 - 7736
  • [6] ENANTIOSELECTIVE ESTERIFICATIONS OF UNSATURATED ALCOHOLS MEDIATED BY A LIPASE PREPARED FROM PSEUDOMONAS SP
    BURGESS, K
    JENNINGS, LD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) : 6129 - 6139
  • [7] Ring closing metathesis of vinyl glycine derivatives
    Campagne, JM
    Ghosez, L
    [J]. TETRAHEDRON LETTERS, 1998, 39 (34) : 6175 - 6178
  • [8] Diels-Alder reactions of 5,6-dihydro-2(1H)-pyridones
    Casamitjana, N
    López, V
    Jorge, A
    Bosch, J
    Molins, F
    Roig, A
    [J]. TETRAHEDRON, 2000, 56 (24) : 4027 - 4042
  • [9] Thirty years of discovering arthropod alkaloids in amphibian skin
    Daly, JW
    [J]. JOURNAL OF NATURAL PRODUCTS, 1998, 61 (01): : 162 - 172
  • [10] Asymmetric synthesis of pentono- and 6-deoxyhexono-δ-lactams via hetero-Diels-Alder reactions with nitroso dienophile
    Defoin, A
    Sarazin, H
    Sifferlen, T
    Strehler, C
    Streith, J
    [J]. HELVETICA CHIMICA ACTA, 1998, 81 (08) : 1417 - 1428
12345