Synthesis of alpha-azido aldehydes stereoselective access to a protected lincosamine analogue

被引:3
|
作者
Sarda, P
Olesker, A
Lukacs, G
机构
[1] CNRS, Inst. Chim. Substances Naturelles
关键词
D O I
10.1016/S0040-4020(97)00240-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of ketone 3 with dichloromethyllithium gave 3. unique branched-chain dichloromethyl sugar 7 whose structure was ascertained by X-ray crystallography. Transformation of 7 in seven steps, involving the key-intermediate alpha-azido-aldehyde 9, afforded the protected lincosamine analogue 14. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:5493 / 5500
页数:8
相关论文
共 50 条
  • [1] SYNTHESIS OF ALPHA-AZIDO ALDEHYDES - STEREOSELECTIVE FORMAL ACCESS TO THE IMMUNOSUPPRESSANT MYRIOCIN
    DELOISY, S
    THANG, TT
    OLESKER, A
    LUKACS, G
    [J]. TETRAHEDRON LETTERS, 1994, 35 (27) : 4783 - 4786
  • [2] Stereoselective access to alpha-azido aldehydes and a new synthetic route to myriocin
    Deloisy, S
    Thang, TT
    Olesker, A
    Lukacs, G
    [J]. BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1996, 133 (06): : 581 - 585
  • [3] SYNTHESIS OF ALPHA-AZIDO NITRILES
    BARONE, AD
    SNITMAN, DL
    WATT, DS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (10): : 2066 - 2068
  • [4] ALPHA-AZIDO ACIDS IN HETEROCYCLIC SYNTHESIS
    GOLDSTEIN, SW
    MCDERMOTT, RE
    MAKOWSKI, MR
    ELLER, C
    [J]. TETRAHEDRON LETTERS, 1991, 32 (40) : 5493 - 5496
  • [5] A GENERAL AND EFFICIENT SYNTHESIS OF ALPHA-AZIDO KETONES
    HOFFMAN, RV
    PATONAY, T
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 376 - ORGN
  • [6] Asymmetric synthesis of enolizable alpha-azido aldehydes from sulfonyl epoxides: Challenges and opportunities
    Anderson, Alexandria
    Allen, Stacey
    Coombs, Thomas
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [7] A GENERAL AND EFFICIENT SYNTHESIS OF ALPHA-AZIDO KETONES
    PATONAY, T
    HOFFMAN, RV
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (10): : 2902 - 2905
  • [8] Use of a novel alpha-hydroxyethylating reagent in the stereoselective synthesis of lincosamine
    vanDelft, FL
    deKort, M
    vanderMarel, GA
    vanBoom, JH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05): : 1883 - 1885
  • [9] Stereoselective access to a-azido aldehydes and a new synthetic route to myriocin
    Deloisy, S.
    Ton That Thang
    Olesker, A.
    Lukacs, G.
    [J]. Bulletin De La Societe Chimique de France, 133 (06):
  • [10] THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS - ELECTROPHILIC AZIDATION OF CHIRAL IMIDE ENOLATES, A PRACTICAL APPROACH TO THE SYNTHESIS OF (R)-ALPHA-AZIDO AND (S)-ALPHA-AZIDO CARBOXYLIC-ACIDS
    EVANS, DA
    BRITTON, TC
    ELLMAN, JA
    DOROW, RL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) : 4011 - 4030