Synthesis of tetrahydropyrans and related heterocycles via prins cyclization; extension to aza-prins cyclization

C Olier, M Kaafarani, S Gastaldi, MP Bertrand - Tetrahedron, 2010 - Elsevier
The Prins reaction 1 is often related to the Kriewitz reaction. 2 The latter leads to unsaturated
alcohol 1 from a-pinene and formaldehyde through a thermal 'ene-rearrangement'(Eq. 1) …

The Prins reaction: Advances and applications

IM Pastor, M Yus - Current Organic Chemistry, 2007 - ingentaconnect.com
The acid-catalyzed alkene-aldehyde condensation, known as the Prins reaction, is
reviewed. Lewis acids, organic acids and supported catalysts have been reported to assist …

Prins cyclization-mediated stereoselective synthesis of tetrahydropyrans and dihydropyrans: an inspection of twenty years

A Budakoti, PK Mondal, P Verma… - Beilstein Journal of …, 2021 - beilstein-journals.org
Functionalized tetrahydropyran (THP) rings are important building blocks and ubiquitous
scaffolds in many natural products and active pharmaceutical ingredients (API). Among …

Ruthenium tetroxide and perruthenate chemistry. Recent advances and related transformations mediated by other transition metal oxo-species

V Piccialli - Molecules, 2014 - mdpi.com
In the last years ruthenium tetroxide is increasingly being used in organic synthesis. Thanks
to the fine tuning of the reaction conditions, including pH control of the medium and the use …

Formal total synthesis of neopeltolide

VV Vintonyak, ME Maier - Organic Letters, 2008 - ACS Publications
A concise synthesis of the core structure of the macrolide neopeltolide was developed
featuring a Prins cyclization to fashion the pyran ring. Key steps in the synthesis of aldehyde …

Brønsted acid-promoted synthesis of common heterocycles and related bio-active and functional molecules

S Ponra, KC Majumdar - RSC advances, 2016 - pubs.rsc.org
Various heterocyclic systems based on natural and unnatural biologically active products
were synthesized by Brønsted acid-promoted cyclization. We have made an attempt to …

A concise stereoselective formal total synthesis of the cytotoxic macrolide (+)-Neopeltolide via Prins cyclization

JS Yadav, GG Krishana, SN Kumar - Tetrahedron, 2010 - Elsevier
A concise stereoselective formal total synthesis of the cytotoxic macrolide (+)-Neopeltolide via
Prins cyclization - ScienceDirect Skip to main contentSkip to article Elsevier logo Journals & …

Stereoselective syntheses of (−)-tetrahydrolipstatin via Prins cyclisations

JS Yadav, MS Reddy, AR Prasad - Tetrahedron letters, 2006 - Elsevier
Stereoselective syntheses of (−)-tetrahydrolipstatin have been achieved via two divergent
approaches through Prins cyclisations as the key steps. PCC mediated oxidative cleavage …

Stereoselective synthesis of anti-1, 3-diol units via Prins cyclisation: application to the synthesis of (−)-sedamine

JS Yadav, MS Reddy, PP Rao, AR Prasad - Tetrahedron letters, 2006 - Elsevier
The scope of the Prins cyclisation, the higher stereoselective synthesis of multisubstituted
tetrahydropyrans from aldehydes and homoallylic alcohols, is expanded. A new approach …

Indium (III)-Catalyzed Asymmetric Hetero-Diels–Alder Reaction of Brassard-Type Diene with Aliphatic Aldehydes

L Lin, Y Kuang, X Liu, X Feng - Organic Letters, 2011 - ACS Publications
A highly diastereo-and enantioselective hetero-Diels–Alder (HDA) reaction of a Brassard-
type diene with aliphatic aldehydes has been developed. The chiral N, N′-dioxide L2/In …