Formal total synthesis of (+)-trehazolin. Application of an asymmetric aldol-olefin metathesis approach to the synthesis of functionalized cyclopentenes

被引:61
作者
Crimmins, MT [1 ]
Tabet, EA [1 ]
机构
[1] Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
关键词
D O I
10.1021/jo015568k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An asymmetric synthesis of the aminocyclopentitol pseudosugar of trehazolin has been completed. The synthesis hinges on an asymmetric aldol-ring closing metathesis strategy to construct the five-membered ring with control of both the relative and absolute stereochemistry.
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页码:4012 / 4018
页数:7
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共 31 条
  • [1] TREHAZOLIN, A NEW TREHALASE INHIBITOR
    ANDO, O
    SATAKE, H
    ITOI, K
    SATO, A
    NAKAJIMA, M
    TAKAHASHI, S
    HARUYAMA, H
    OHKUMA, Y
    KINOSHITA, T
    ENOKITA, R
    [J]. JOURNAL OF ANTIBIOTICS, 1991, 44 (10) : 1165 - 1168
  • [2] MANNOSTATIN-A AND MANNOSTATIN-B - NEW INHIBITORS OF ALPHA-D-MANNOSIDASE, PRODUCED BY STREPTOVERTICILLIUM-VERTICILLUS VAR QUINTUM ME3-AG3 - TAXONOMY, PRODUCTION, ISOLATION, PHYSICOCHEMICAL PROPERTIES AND BIOLOGICAL-ACTIVITIES
    AOYAGI, T
    YAMAMOTO, T
    KOJIRI, K
    MORISHIMA, H
    NAGAI, M
    HAMADA, M
    TAKEUCHI, T
    UMEZAWA, H
    [J]. JOURNAL OF ANTIBIOTICS, 1989, 42 (06) : 883 - 889
  • [3] A FACILE PREPARATION OF AROMATIC ANION RADICALS BY ULTRASOUND IRRADIATION
    AZUMA, T
    YANAGIDA, S
    SAKURAI, H
    SASA, S
    YOSHINO, K
    [J]. SYNTHETIC COMMUNICATIONS, 1982, 12 (02) : 137 - 140
  • [4] Synthesis and biological activity of natural aminocyclopentitol glycosidase inhibitors: Mannostatins, trehazolin, allosamidins, and their analogues
    Berecibar, A
    Grandjean, C
    Siriwardena, A
    [J]. CHEMICAL REVIEWS, 1999, 99 (03) : 779 - 844
  • [5] Synthesis of trehazolin from D-glucose
    Boiron, A
    Zillig, P
    Faber, D
    Giese, B
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (17) : 5877 - 5882
  • [6] Asymmetric aldol additions:: Use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones
    Crimmins, MT
    King, BW
    Tabet, EA
    Chaudhary, K
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) : 894 - 902
  • [7] An efficient asymmetric approach to carbocyclic nucleosides: Asymmetric synthesis of 1592U89, a potent inhibitor of HIV reverse transcriptase
    Crimmins, MT
    King, BW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (13) : 4192 - 4193
  • [8] Asymmetric aldol additions with titanium enolates of acyloxazolidinethiones: Dependence of selectivity on amine base and Lewis acid stoichiometry
    Crimmins, MT
    King, BW
    Tabet, EA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (33) : 7883 - 7884
  • [9] An improved synthetic preparation of 3-butenal
    Crimmins, MT
    Kirincich, SJ
    Wells, AJ
    Choy, AL
    [J]. SYNTHETIC COMMUNICATIONS, 1998, 28 (19) : 3675 - 3679
  • [10] de Gracia IS, 1999, ORG LETT, V1, P1705