Synthetic approaches to the manumycin A, B and C antibiotics: The first total synthesis of (+)-manumycin A

被引:43
作者
Alcaraz, L
Macdonald, G
Ragot, J
Lewis, NJ
Taylor, RJK [1 ]
机构
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
[2] SmithKline Beecham Pharmaceut, Tonbridge TN11 9AN, Kent, England
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/S0040-4020(98)00879-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of Manumycin A, as its (+)-enantiomer, is reported. The synthetic route features an asymmetric epoxidation (based on Wynberg's chiral phase transfer methodology) for the preparation of the key epoxyquinol nucleus, and a further demonstration of the utility of the Stille reaction for the construction of the Manumycin lower side chain. This synthesis of Manumycin A corrects the original stereochemical assignment and confirms the syn-hydroxy epoxide arrangement. The first syntheses of the quinones obtained by the oxidative degradation of Manumycins A-C are also described. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3707 / 3716
页数:10
相关论文
共 35 条
  • [1] The first synthesis of the Streptomyces derived antibiotic U-62162
    Alcaraz, L
    Taylor, RJK
    [J]. CHEMICAL COMMUNICATIONS, 1998, (10) : 1157 - 1158
  • [2] Manumycin A: Synthesis of the (+)-enantiomer and revision of stereochemical assignment
    Alcaraz, L
    Macdonald, G
    Ragot, JP
    Lewis, N
    Taylor, RJK
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (11) : 3526 - 3527
  • [3] ASYMMETRIC EPOXIDATION OF CYCLIC ENONES UNDER CHIRAL PHASE-TRANSFER CONDITIONS
    BABA, N
    ODA, J
    KAWAGUCHI, M
    [J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1986, 50 (12): : 3113 - 3117
  • [4] BUZZETTI F, 1963, PHARM ACTA HELV, V38, P871
  • [5] SOME ASPECTS OF THE STEREOCHEMISTRY AND BIOSYNTHESIS OF ASUKAMYCIN
    CHO, HG
    SATTLER, I
    BEALE, JM
    ZEECK, A
    FLOSS, HG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (27) : 7925 - 7928
  • [6] PREPARATION OF TRANS-1,2-BIS(TRI-NORMAL-BUTYLSTANNYL)ETHYLENE
    COREY, EJ
    WOLLENBERG, RH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (25) : 3788 - 3789
  • [7] Farina V., 1997, ORG REACT, V50, P1, DOI DOI 10.1002/0471264180.or050.01
  • [8] Natural products derived from unusual variants of the shikimate pathway
    Floss, HG
    [J]. NATURAL PRODUCT REPORTS, 1997, 14 (05) : 433 - 452
  • [9] GAGE JR, 1990, ORG SYNTH, V68, P77
  • [10] Acetal and ketal deprotection using montmorillonite K10: The first synthesis of syn-4,8-dioxatricyclo[5.1.0.0(3,5)]-2,6-octanedione
    Gautier, ECL
    Graham, AE
    McKillop, A
    Standen, SP
    Taylor, RJK
    [J]. TETRAHEDRON LETTERS, 1997, 38 (11) : 1881 - 1884