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 …

Pd-catalyzed enantioselective aerobic oxidation of secondary alcohols: applications to the total synthesis of alkaloids

S Krishnan, JT Bagdanoff, DC Ebner… - Journal of the …, 2008 - ACS Publications
Enantioselective syntheses of the alkaloids (−)-aurantioclavine,(+)-amurensinine,(−)-
lobeline, and (−)-and (+)-sedamine are described. The syntheses demonstrate the …

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 …

CeCl3· 7H2O/AcCl-catalyzed Prins–Ritter reaction sequence: a novel synthesis of 4-amido tetrahydropyran derivatives

JS Yadav, BVS Reddy, GN Kumar, GM Reddy - Tetrahedron letters, 2007 - Elsevier
Homoallylic alcohols, carbonyl compounds and nitriles undergo a smooth tandem Prins–
Ritter type cyclization in the presence of CeCl3· 7H2O/AcCl at ambient temperature 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 & …

Stereodivergent synthesis of piperidine alkaloids by ring‐rearrangement metathesis/reductive lactam alkylation of nitroso Diels–Alder cycloadducts

G Vincent, D Karila, G Khalil… - … A European Journal, 2013 - Wiley Online Library
A general methodology for the stereoselective synthesis of 2‐(2‐hydroxyalkyl) piperidine
alkaloids by ring‐rearrangement metathesis of nitroso Diels–Alder cycloadducts is reported …

The stereoselective total synthesis of xestodecalactone C and epi-sporostatin via the Prins cyclisation

JS Yadav, N Thrimurtulu, KU Gayathri, BVS Reddy… - Tetrahedron …, 2008 - Elsevier
The stereoselective total synthesis of xestodecalactone C and epi-sporostatin via the Prins
cyclisation - ScienceDirect Skip to main contentSkip to article Elsevier logo Journals & …

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 …