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

页数：35

共 50 条

[21] Racemization in prins cyclization reactions
Jasti, Ramesh
Rychnovsky, Scott D.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (41) : 13640 - 13648
[22] Recent Advances in the Prins Cyclization
Greco, Sandro Jose
Fiorot, Rodolfo Goetze
Lacerda, Valdemar, Jr.
dos Santos, Reginaldo Bezerra
ALDRICHIMICA ACTA, 2013, 46 (02) : 59 - 67
[23] Progress in the construction of cyclooctanoid systems: New approaches and applications to natural product syntheses
Mehta, G
Singh, V
CHEMICAL REVIEWS, 1999, 99 (03) : 881 - 930
[24] Progress in the Construction of Cyclooctanoid Systems: New Approaches and Applications to Natural Product Syntheses
Mehta, Goverdhan
Singh, Vishwakarma
Chemical Reviews, 99 (03): : 881 - 930
[25] Synthesis of tetrahydropyrans and related heterocycles via prins cyclization; extension to aza-prins cyclization
Olier, Clarisse
Kaafarani, Mustapha
Gastaldi, Stephane
Bertrand, Michele P.
TETRAHEDRON, 2010, 66 (02) : 413 - 445
[26] The use of furans in natural product syntheses
Wong, HNC
Yu, P
Yick, CY
PURE AND APPLIED CHEMISTRY, 1999, 71 (06) : 1041 - 1044
[27] Thapsigargin: a promising natural product with diverse medicinal potential - a review of synthetic approaches and total syntheses
Suresh, Anisha
Bagchi, Dibyojeet
Kaliappan, Krishna P.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (43) : 8551 - 8569
[28] Syntheses of Polycyclic Tetrahydrofurans by Cascade Reactions Consisting of Five-Membered Ring Selective Prins Cyclization and Friedel-Crafts Cyclization
Sakata, Yuki
Yasui, Eiko
Takatori, Kazuhiko
Suzuki, Yuji
Mizukami, Megumi
Nagumo, Shinji
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (16): : 9103 - 9118
[29] Development of synthetic methods for 4-substituted indoles and their applications for the syntheses of natural products
Yamada, F
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 2000, 120 (04): : 363 - 373
[30] ORGANIC-PHOTOCHEMISTRY .15. APPLICATIONS OF PHOTOCYCLOADDITION REACTIONS IN NATURAL PRODUCT SYNTHESES
DILLING, WL
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1977, 25 (06) : 605 - 621

← 1 2 3 4 5 →