Chemoenzymatic approaches to the montanine alkaloids: A total synthesis of (+)-brunsvigine

被引:56
|
作者
Banwell, Martin G. [1 ]
Kokas, Okanya J. [1 ]
Willis, Anthony C. [1 ]
机构
[1] Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia
关键词
D O I
10.1021/ol071344y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The readily available and enzymatically derived cis-1,2-dihydrocatechols 3a and 3b have been elaborated over 17 steps, including a novel radical addition/elimination sequence, into the enantiomer, (+)-1, of the montanine alkaloid brunsvigine [(-)-1].
引用
收藏
页码:3503 / 3506
页数:4
相关论文
共 50 条
  • [31] INDOLE ALKALOIDS - ENANTIOSELECTIVE SYNTHESIS OF (-)-ALLOYOHIMBANE BY A CHEMOENZYMATIC APPROACH
    RIVA, R
    BANFI, L
    DANIELI, B
    GUANTI, G
    LESMA, G
    PALMISANO, G
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (04) : 299 - 300
  • [32] ENANTIOSELECTIVE SYNTHESIS OF ALKALOIDS AND CARBOHYDRATES VIA CHEMOENZYMATIC METHODS
    HUDLICKY, T
    PURE AND APPLIED CHEMISTRY, 1994, 66 (10-11) : 2067 - 2070
  • [33] Synthetic Approaches to Tricyclic Aminoketones in the Total Synthesis of Aspidosperma and Kopsia Alkaloids
    Wang, Nengzhong
    Jiang, Xuefeng
    CHEMICAL RECORD, 2021, 21 (02): : 295 - 314
  • [34] UTILIZATION OF AMINO-ACIDS IN APPROACHES TO THE TOTAL SYNTHESIS OF INDOLIZIDINE ALKALOIDS
    SIBI, MP
    CHRISTENSEN, JW
    RENHOWE, PA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 199 : 235 - ORGN
  • [35] ORGN 549-Cascade approaches to the total synthesis of the lepadin alkaloids
    Thompson, Sam
    Smith, M. D.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 236
  • [36] Chemoenzymatic formal total synthesis of (-)-bestatin
    Feske, BD
    Stewart, JD
    TETRAHEDRON-ASYMMETRY, 2005, 16 (18) : 3124 - 3127
  • [37] APPROACHES TO THE TOTAL SYNTHESIS OF MONTANINE-TYPE ALKALOIDS - A 1ST SYNTHESIS OF (+/-)-4A,11A-CIS-11,11A-ANTI-5,11-METHANOMORPHANTHRIDINE AND ITS TRANS-ISOMER
    HOSHINO, O
    ISHIZAKI, M
    SAITO, K
    YUMOTO, K
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (05) : 420 - 421
  • [38] Total and Chemoenzymatic Synthesis of Seongsanamide E
    Brazeau-Henrie, Jordan T.
    Paquette, Andre R.
    O'Rourke, Allison Q. .
    Darnowski, Michael G.
    Boddy, Christopher N.
    ORGANIC LETTERS, 2022, 24 (35) : 6369 - 6373
  • [39] Total and chemoenzymatic synthesis of the lipodepsipeptide rhizomide A
    Lepetit, Corinne A.
    Paquette, Andre R.
    Brazeau-Henrie, Jordan T.
    Boddy, Christopher N.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2023, 96
  • [40] Synthesis of aza bicyclic enones via anionic cyclization: Application to the total synthesis of (-)-brunsvigine
    Sha, CK
    Hong, AW
    Huang, CM
    ORGANIC LETTERS, 2001, 3 (14) : 2177 - 2179