Modular and stereoselective formal synthesis of MeBmt, an unusual amino acid constituent of cyclosporin A

被引：4
|
作者：
Raghavan, S [1 ]
Rasheed, MA [1 ]
机构：
[1] Indian Inst Chem Technol, Organ Div 1, Hyderabad 500007, Andhra Pradesh, India
来源：
TETRAHEDRON | 2004年 / 60卷 / 13期
关键词：
MeBmt; sulfoxide; neighbouring group participation; bromohydrin;
D O I：
10.1016/j.tet.2004.01.088
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convergent, flexible and stereoselective formal synthesis of MeBmt, the nonproteinogenic amino acid constituent of cyclosporin A is disclosed. The sulfinyl moiety has been exploited as the internal nucleophile to stereo- and regioselectively functionalize, an allylic carbamate. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3059 / 3065
页数：7
相关论文
共 50 条
  • [41] Stereoselective amino acid synthesis by synergistic photoredox-pyridoxal radical biocatalysis
    Cheng, Lei
    Li, Dian
    Mai, Binh Khanh
    Bo, Zhiyu
    Cheng, Lida
    Liu, Peng
    Yang, Yang
    SCIENCE, 2023, 381 (6656) : 444 - 451
  • [42] Stereoselective Synthesis of New Ferrocene-Derived Amino Acid Building Blocks
    Hunold, Andrea
    Neundorf, Ines
    James, Philippe
    Neudoerfl, Joerg
    Schmalz, Hans-Guenther
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (26) : 4429 - 4440
  • [43] Stereoselective synthesis of a conformationally restricted beta-hydroxy-gamma-amino acid
    Xiao, D
    Carroll, PJ
    Mayer, SC
    Pfizenmayer, AJ
    Joullie, MM
    TETRAHEDRON-ASYMMETRY, 1997, 8 (18) : 3043 - 3046
  • [44] Hydrolases in the Stereoselective Synthesis of N-Heterocyclic Amines and Amino Acid Derivatives
    Busto, Eduardo
    Gotor-Fernandez, Vicente
    Gotor, Vicente
    CHEMICAL REVIEWS, 2011, 111 (07) : 3998 - 4035
  • [45] STEREOSELECTIVE SYNTHESIS AND PEPTIDE INCORPORATION OF A PYRIDOXAL COENZYME AMINO-ACID CHIMERA
    IMPERIALI, B
    ROY, RS
    JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06): : 1891 - 1894
  • [46] Memory of chirality in the stereoselective synthesis of β-lactams:: importance of the starting amino acid derivative
    Bonache, MA
    Gerona-Navarro, G
    García-Aparicio, C
    Alías, M
    Martín-Martínez, M
    García-López, MT
    López, P
    Cativiela, C
    González-Muñiz, R
    TETRAHEDRON-ASYMMETRY, 2003, 14 (15) : 2161 - 2169
  • [47] STEREOSELECTIVE SYNTHESIS OF (2S,3S,4R)-4-AMINO-3-HYDROXY-2-METHYL-PENTANOIC ACID, AN AMINO-ACID CONSTITUENT OF BLEOMYCIN, BY ALDOL CONDENSATION
    NARITA, M
    OTSUKA, M
    KOBAYASHI, S
    OHNO, M
    UMEZAWA, Y
    MORISHIMA, H
    SAITO, SI
    TAKITA, T
    UMEZAWA, H
    TETRAHEDRON LETTERS, 1982, 23 (05) : 525 - 528
  • [48] Stereoselective Formal Synthesis of (+)-Allokainic Acid via Thiol-Mediated Acyl Radical Cyclization
    Yamada, Ken-ichi
    Sato, Tomohiro
    Hosoi, Masaki
    Yamamoto, Yasutomo
    Tomioka, Kiyoshi
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2010, 58 (11) : 1511 - 1516
  • [49] Design and synthesis of hexahydro pyrene containing unusual α-amino acid derivatives
    Sambasivarao Kotha
    Vidyasagar Gaikwad
    Saima Ansari
    Journal of Chemical Sciences, 135
  • [50] Design and synthesis of hexahydro pyrene containing unusual α-amino acid derivatives
    Kotha, Sambasivarao
    Gaikwad, Vidyasagar
    Ansari, Saima
    JOURNAL OF CHEMICAL SCIENCES, 2023, 135 (02)
12345