Synthetic Applications of Prins Cyclization in Natural Product Syntheses

被引：5
|
作者：
Tadiparthi, Krishnaji [1 ]
Roy, Allen [1 ]
Sakirolla, Raghavendra [2 ,3 ]
Reddy, B. V. Subba [3 ]
Yadav, Jhillu Singh [3 ,4 ]
机构：
[1] CHRIST Deemed Univ, Dept Chem, Hosur Rd, Bangalore 560029, Karnataka, India
[2] Cent Univ Karnataka, Dept Chem, Gulbarga 585367, Karnataka, India
[3] CSIR Indian Inst Chem Technol, Fluoro & Agrochem, Hyderabad 500007, India
[4] Indrashil Univ, Sch Sci, Mehsana 382740, Gujarat, India
来源：
CHEMICAL RECORD | 2022年 / 22卷 / 08期
关键词：
Total synthesis; Natural products; Prins reaction; Tetrahyropyran; Chiral pool; STEREOSELECTIVE TOTAL-SYNTHESIS; UNITS;
D O I：
10.1002/tcr.202200044
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The natural products having tetrahydropyran unit with multiple chiral centers serve as magnificent building blocks for various active pharmaceutical ingredients (APIs). 'Prins cyclization is one of the wonderful strategies to construct tetrahydropyran unit stereoselectively in asymmetric synthesis. In this account, we discuss our research efforts toward the synthesis of various natural products from the past two decades (2005-2020) by using Prins cyclization as a key step. Further, the synthetic utility of this reaction was investigated and well demonstrated on various molecules successfully.
引用
收藏
页数：35
相关论文
共 50 条
  • [1] Prins-Type Cyclization Reactions in Natural Product Synthesis
    Han, Xun
    Peh, GuangRong
    Floreancig, Paul E.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (07) : 1193 - 1208
  • [2] Tandem Prins-Schmidt reaction: Applications toward natural product synthesis
    Meyer, Angelica
    Aube, Jeffrey
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
  • [3] Syntheses of Bufospirostenin A and Ophiopogonol A by a Conformation-Controlled Transannular Prins Cyclization
    Yang, Peicheng
    Li, Yan-Yu
    Tian, Hailong
    Qian, Gan-Lu
    Wang, Yun
    Hong, Xin
    Gui, Jinghan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (39) : 17769 - 17775
  • [4] Asymmetric Syntheses of (-)-Pentazocine and (-)-Eptazocine through an Aza-Prins Cyclization
    Chen, Qiang
    Huo, Xing
    Yang, Zhen
    She, Xuegong
    CHEMISTRY-AN ASIAN JOURNAL, 2012, 7 (11) : 2543 - 2546
  • [5] Synthetic applications (total synthesis and natural product synthesis)
    Tohma, H
    Kita, Y
    HYPERVALENT IODINE CHEMISTRY: MODERN DEVELOPMENTS IN ORGANIC SYNTHESIS, 2003, 224 : 209 - 248
  • [6] Alkynyl Prins and Alkynyl Aza-Prins Annulations: Scope and Synthetic Applications
    Abdul-Rashed, Shukree
    Holt, Connor
    Frontier, Alison J.
    SYNTHESIS-STUTTGART, 2020, 52 (14): : 1991 - 2007
  • [7] Focused Update on the Prins Reaction and the Prins Cyclization
    Pastor, Isidro M.
    Yus, Miguel
    CURRENT ORGANIC CHEMISTRY, 2012, 16 (10) : 1277 - 1312
  • [8] SYNTHETIC APPLICATIONS OF THE NAZAROV CYCLIZATION
    HARDING, KE
    WILSON, JM
    TSENG, CY
    CLEMENT, KS
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1979, (SEP): : 39 - 39
  • [9] The Curtius rearrangement: mechanistic insight and recent applications in natural product syntheses
    Ghosh, Arun K.
    Sarkar, Anindya
    Brindisi, Margherita
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (12) : 2006 - 2027
  • [10] Anthrol reductases: discovery, role in biosynthesis and applications in natural product syntheses
    Rajput, Anshul
    Manna, Tanaya
    Husain, Syed Masood
    NATURAL PRODUCT REPORTS, 2023, 40 (10) : 1672 - 1686
12345