A Domino Dearomative ipso-Annulation/Desymmetrization Approach: Stereoselective Access to Tricyclic Alkaloid Skeletons

被引：6
作者：
Reddy, Chada Raji [1 ,2 ]
Prasad, Aratikumari Suresh [1 ,2 ]
Ajaykumar, Uprety [1 ,2 ]
机构：
[1] CSIR Indian Inst Chem Technol, Dept Organ Synth & Proc Chem, Hyderabad 500007, Telangana, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, Uttar Pradesh, India
来源：
ORGANIC LETTERS | 2024年 / 26卷 / 23期
关键词：
ENANTIOSELECTIVE DESYMMETRIZATION; QUATERNARY STEREOCENTERS; STEREOGENIC CENTERS; N-BENZYLACRYLAMIDES; SPIROCYCLIZATION; CYCLIZATION; CYCLOHEXADIENONES; CONSTRUCTION;
D O I：
10.1021/acs.orglett.4c01407
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we reveal an unprecedented domino annulation of N-benzyl-acrylamides with 1,3-dicarbonyls for the assembly of fused tricyclic alkaloid frameworks incorporating a spirocycle via an alkylation/dearomative ipso-annulation/Michael addition (desymmetrization) sequence. This conversion involves three carbon-carbon bond formations, generating four chiral carbons, including three quaternary carbon centers, in a single diastereomer in one pot under identical reaction conditions. The synthetic potential of this atom-economic method is illustrated by modifications of the functional groups present in the products obtained.
引用
收藏
页码：4904 / 4909
页数：6
相关论文
共 8 条
  • [1] Electrochemical Domino Sulfonylation/Dearomative ipso-Annulation of 2-Alkynyl Biaryls to Access Spiro(indenyl)cyclohexadienones
    Reddy, Chada Raji
    Nair, Karna
    Vinaya, Puthiya Purayil
    Ajaykumar, Uprety
    Gree, Rene
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (48)
  • [2] A dearomative ipso-iodocyclization/desymmetrization sequence leading to optically active tricyclic piperazine scaffolds
    Okitsu, Takashi
    Horike, Arisa
    Shimazawa, Natsumi
    Wada, Akimori
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (18) : 3501 - 3511
  • [3] Desymmetrization of Cyclohexadienones via [3+2]/[2+1] Domino Annulation: Access to Cyclopropane Fused Tricyclic Enones
    Zhu, Yannan
    Wang, Sen
    Fang, Bo
    Li, Qiuyun
    Qi, Gang
    Han, Zhongfei
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (13) : 2939 - 2944
  • [4] Access to Diverse Seleno-spirocyclohexadienones via Ag(II)- Catalyzed Selenylative ipso-Annulation with Se and Boronic Acids
    Reddy, Chada Raji
    Subbarao, Muppidi
    Kolgave, Dattahari H.
    Ajaykumar, Uprety
    Vinaya, Puthiya Purayil
    ACS OMEGA, 2022, 7 (42): : 38045 - 38052
  • [5] Stereoselective Domino Rearrangement peri-Annulation of Cinchona Alkaloid Derivatives with 8-Bromo-1-naphthyl Grignard
    Boratynski, Przemyslaw J.
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (17) : 11602 - 11607
  • [6] Dearomative ipso-Cyclization to Spiropseudoindoxyls: An Extendable Approach To Access Indolo[3,2-c]quinolinones and Isocryptolepine
    Reddy, Chada Raji
    Theja, Agnuru
    Srinivasu, Ejjirotu
    Subbarao, Muppidi
    ORGANIC LETTERS, 2023, 26 (01) : 68 - 72
  • [7] CAN-Promoted Thiolative ipso-Annulation of Unactivated N-Benzyl Acrylamides: Access to SCN/SCF3/SO2Ar Containing Azaspirocycles
    Reddy, Chada Raji
    Ajaykumar, Uprety
    Kolgave, Dattahari H.
    Ramesh, Remya
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (11) : 7117 - 7127
  • [8] Synthesis of Alkaloid-Mimicking Tricyclic Skeletons by Diastereo- and Regioselective Ugi/ipso-Cyclization/Aza-Michael Cascade Reaction in One-Pot
    Yugandhar, D.
    Kuriakose, Sunu
    Nanubolu, Jagadeesh Babu
    Srivastava, Ajay Kumar
    ORGANIC LETTERS, 2016, 18 (05) : 1040 - 1043
1