We have developed a mild, intramolecular intercepted Meyer-Schuster (M-S) rearrangement for the synthesis of 2-acylfurans from corresponding cis-6-hydroxyhex-2-en-4-ynals. This reaction was found to be very general, and the starting materials are easily accessible. By this methodology the first synthesis of deoxy-nor-abiesesquine B, a sesquiterpene, was also achieved in three steps. The concept of adding two nucleophiles during the M-S rearrangement was introduced. © 2015 American Chemical Society.

Beeraiah Baire

Department Of Chemistry

Prabhakararao Tharra

MEYER-SCHUSTER REARRANGEMENT

Sesquiterpenes

Organic compounds

aldehyde

electrophile

furan derivative

hydronium ion

natural product

nucleophile

sesquiterpene

article

Mass spectrometry

methodology

Nuclear magnetic resonance spectroscopy

proton transport

synthesis

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IIT Madras

Journal of Organic Chemistry

The Meyer–Schuster rearrangement of propargylic alcohols is a transformation in organic synthesis known for almost a century. The products of this reaction—α,β-enones and their α-functionalized units—are highly important functional groups for various synthetic transformations. Two modifications of this classical reaction, which involves interception of the intermediate allenol (or its equivalent) by either electrophiles or nucleophiles, have attracted the attention of synthetic organic chemists. This Focus Review provides a detailed description of the development of these two strategies. © 2018 Wiley-VCH Verlag GmbH &amp; Co. KGaA, Weinheim

Asian Journal of Organic Chemistry

Intercepted Meyer–Schuster Rearrangements in Organic Synthesis

A mild cascade approach for the generation of 2-(α-hydroxyacyl)pyrroles under Ag(I) catalysis has been reported. This strategy involves a 5-exo-dig cyclization of insitu generated imines from 6-hydroxyhex-2-en-4-ynals and primary amines followed by oxidation. The reaction is very general for propargylic alcohols, tethers and primary amines. Efficient synthesis of core structures of pyrrole based bioactive natural products have also been achieved. Control experiments revealed the fact that, presence of excess oxygen and water may favor the competitive formation of the furans over the pyrroles. © 2017 Wiley-VCH Verlag GmbH &amp; Co. KGaA, Weinheim

ChemistrySelect

Ag(I) Catalyzed Cascade Approach to 2-(α-Hydroxyacyl)pyrroles

Structure of TYK2 with inhibitor 16: 3-azanyl-5-[(2~{S})-3-methylbutan-2-yl]-7-[1-methyl-5-(2-oxidanylpropan-2-yl)pyrazol-3-yl]-1~{H}-pyrazolo[4,3-c]pyridin-4-one

European Journal of Organic Chemistry

Alkynylation of Aldehydes and Ketones Using the Bu4NOH/H2O/DMSO Catalytic Composition: A Wide-Scope Methodology

Angewandte Chemie International Edition

Merging Synthesis and Enantioselective Functionalization of Indoles by a Gold-Catalyzed Asymmetric Cascade Reaction

Enantioselective Fluoroamination: 1,4-Addition to Conjugated Dienes Using Anionic Phase-Transfer Catalysis

Copper-Catalyzed Arylative Meyer-Schuster Rearrangement of Propargylic Alcohols to Complex Enones Using Diaryliodonium Salts

Mild Approach to 2-Acylfurans via Intercepted Meyer-Schuster Rearrangement of 6-Hydroxyhex-2-en-4-ynals

Journal	Data powered by TypesetJournal of Organic Chemistry
Publisher	Data powered by TypesetAmerican Chemical Society
ISSN	00223263
Open Access	No