(±)-cis-(6-Ethyl-tetrahydropyran-2-yl)-formic acid: a novel substance with antinociceptive properties

LSM Miranda, BG Marinho, SG Leitão… - Bioorganic & medicinal …, 2004 - Elsevier
We described in this paper the first synthesis to the (±) cis (6-ethyl-tetrahydropyran-2-yl)
formic acid (1) using the very efficient Prins cyclization reaction as strategy to construction of …

Design, Prins-cyclization reaction promoting diastereoselective synthesis of 10 new tetrahydropyran derivatives and in vivo antinociceptive evaluations

SL Capim, PHP Carneiro, PC Castro… - European journal of …, 2012 - Elsevier
We described in this article the very efficient 2, 6-cis ou 2, 4, 6-cis diastereoselective
synthesis (2 or 3 steps, 62–65% global yields) from Prins-cyclization reaction as synthetic …

First enantioselective synthesis of (-)-(2S, 6S)-(6-ethyltetrahydropyran-2-yl) formic acid

LSM Miranda, BA Meireles, JS Costa, VLP Pereira… - Synlett, 2005 - thieme-connect.com
We describe in this letter the first enantioselective synthesis of (-)-(2S, 6S)-(6-
ethyltetrahydropyran-2-yl) formic acid (2) in five steps (30% overall yield, 87% ee), from the …

Aminol initiated Prins cyclization for the synthesis of octahydro-1H-pyrano [3, 4-c] pyridine and hexahydro-1H-furo [3, 4-c] pyrrole derivatives

BVS Reddy, SG Reddy, MR Reddy, B Sridhar… - Tetrahedron letters, 2014 - Elsevier
Various aldehydes undergo smooth coupling with a branched homoallylic alcohol
appended N-tosyl amine (1 & 3) in the presence of 10 mol% BF 3· OEt 2 at room …

Changing the reaction pathway of Silyl-Prins cyclization by switching the lewis acid: Application to the synthesis of an antinociceptive compound

C Díez-Poza, L Fernández-Peña… - The Journal of …, 2023 - ACS Publications
Developing new procedures for the synthesis of tetrahydropyrans in a very stereoselective
manner is of great importance for the synthesis of THP-containing natural products. Here, we …

Synthetic Applications of Prins Cyclization in Natural Product Syntheses

K Tadiparthi, A Roy, R Sakirolla… - The Chemical …, 2022 - Wiley Online Library
The natural products having tetrahydropyran unit with multiple chiral centers serve as
magnificent building blocks for various active pharmaceutical ingredients (APIs).'Prins …

Diastereoselective synthesis of dihydropyrans via Prins cyclization of enol ethers: total asymmetric synthesis of (+)-civet cat compound

S Sultana, K Indukuri, MJ Deka… - The Journal of Organic …, 2013 - ACS Publications
Diastereoselective Synthesis of Dihydropyrans via Prins Cyclization of Enol Ethers: Total
Asymmetric Synthesis of (+)-Civet Cat Compound | The Journal of Organic Chemistry ACS ACS …

Iodine as a versatile reagent for the Prins-cyclization: an expeditious synthesis of 4-iodotetrahydropyran derivatives

JS Yadav, BVS Reddy, GN Kumar, T Swamy - Tetrahedron letters, 2007 - Elsevier
Iodine is found to be an efficient reagent for the coupling of homoallylic alcohols with
aldehydes under mild conditions to produce 4-iodotetrahydropyran derivatives in excellent …

InCl3-promoted a novel Prins cyclization for the synthesis of hexahydro-1H-furo [3, 4-c] pyran derivatives

BVS Reddy, M Sreelatha, C Kishore, P Borkar… - Tetrahedron …, 2012 - Elsevier
(2-(4-Methoxyphenyl)-4-methylenetetrahydrofuran-3-yl) methanol reacts smoothly with
different aldehydes in the presence of InCl3 at an ambient temperature to afford a novel …

The Stereoselective Total Synthesis of (6S)‐5,6‐Dihydro‐6‐[(2R)‐2‐hydroxy‐6‐phenylhexyl]‐2H‐pyran‐2‐one via Prins Cyclization

JS Yadav, D Chandrakanth, YG Rao… - Helvetica Chimica …, 2010 - Wiley Online Library
The stereoselective total synthesis of an antiproliferative and antifungal α‐pyrone natural
product (6S)‐5, 6‐dihydro‐6‐[(2R)‐2‐hydroxy‐6‐phenylhexyl]‐2H‐pyran‐2‐one is …