A Facile Total Synthesis of Hainanensine via an Unusual Rearrangement-Annulation Cascade

被引：19
|
作者：
Zhang, Zhi-Wei [1 ]
Li, Wei-Dong Z. [1 ,2 ]
机构：
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 08期
关键词：
CEPHALOTAXINE;
D O I：
10.1021/ol1003324
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A facile total synthesis of hainanensine (1), a structurally unique Cephalotaxus alkaloid, via an effective acid-mediated rearrangement/ Friedel Crafts annulation cascade (a7a/7b -> 8a/8b), is described.
引用
收藏
页码：1649 / 1651
页数：3
相关论文
共 50 条
  • [1] Synthesis of Trisubstituted Oxazoles via Aryne Induced [2,3] Sigmatropic Rearrangement-Annulation Cascade
    Gaykar, Rahul N.
    Deswal, Shiksha
    Guin, Avishek
    Bhattacharjee, Subrata
    Biju, Akkattu T.
    ORGANIC LETTERS, 2022, 24 (23) : 4145 - 4150
  • [2] Formal total synthesis of (±)-trichodiene via Claisen rearrangement and Robinson annulation
    Jung, Jae-Chul
    Jung, Young-Jo
    Park, Oee-Sook
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2008, 63 (03): : 293 - 297
  • [3] Total synthesis of (±)-tremulenolide A and (±)-tremulenediol A via a stereoselective cyclopropanation/cope rearrangement annulation strategy
    Davies, HML
    Doan, BD
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (03): : 657 - 660
  • [4] Total synthesis of (±)-strychnine via a [4+2]-cycloaddition/rearrangement cascade
    Zhang, Hongjun
    Boonsombat, Jutatip
    Padwa, Albert
    ORGANIC LETTERS, 2007, 9 (02) : 279 - 282
  • [5] SEQUENTIAL REARRANGEMENT-ANNULATION OF ISOXAZOLINE-5-SPIROCYCLOPROPANES - TOTAL SYNTHESIS OF (+/-)-DELTA-9(11)-19-NOR-10-AZA-TESTOSTERONE
    BELLE, C
    CARDELLI, A
    GUARNA, A
    TETRAHEDRON LETTERS, 1991, 32 (44) : 6395 - 6398
  • [6] Pyridone Annulation via Tandem Curtius Rearrangement/6π-Electrocyclization: Total Synthesis of (-)-Lyconadin C
    Cheng, Xiayun
    Waters, Stephen P.
    ORGANIC LETTERS, 2013, 15 (16) : 4226 - 4229
  • [7] Total Synthesis of Tetracyclic Spirooxindole Alkaloids via a Double Oxidative Rearrangement/Cyclization Cascade
    Wang, Xin
    Zhang, Mengjiao
    Liu, Xiaolei
    Lou, Mingliang
    Li, Gen
    Qi, Xiangbing
    ORGANIC LETTERS, 2024, 26 (04) : 824 - 828
  • [8] A Concise Total Synthesis of (-)-Quinocarcin via Aryne Annulation
    Allan, Kevin M.
    Stoltz, Brian M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (51) : 17270 - +
  • [9] Stereoselective Total Synthesis of Aminoiminohexitols via Carbamate Annulation
    Win-Mason, Anna L.
    Jongkees, Seino A. K.
    Withers, Stephen G.
    Tyler, Peter C.
    Timmer, Mattie S. M.
    Stocker, Bridget L.
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (23): : 9611 - 9621
  • [10] Total synthesis of A-315675 based on the cascade Overman rearrangement
    Momose, Takayuki
    Hama, Naoto
    Higashino, Chiharu
    Sato, Hideyuki
    Chida, Noritaka
    TETRAHEDRON LETTERS, 2008, 49 (08) : 1376 - 1379
12345