Synthesis, Table of Contents

Synthesis 2023; 55(17): 2757-2772
DOI: 10.1055/s-0042-1751458

paper

Special Issue Honoring Prof. Guoqiang Lin’s Contributions to Organic Chemistry

Divergent Synthesis of Isochroman-4-ols, 1,3-Dihydroisobenzofurans, and Tetrahydro-2H-indeno[2,1-b]furan-2-ones via Epoxidation/Cyclization Strategy of (E)-(2-Stilbenyl/Styrenyl)methanols

Jira Jongcharoenkamol

^aProgram in Chemical Sciences, Chulabhorn Graduate Institute, 906 Kamphaeng Phet 6 Road, Laksi, Bangkok, Thailand 10210, Thailand

^bLaboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6 Road, Laksi, Bangkok, Thailand 10210, Thailand

^cDepartment of Pharmaceutical Chemistry and Pharmacognosy, Faculty of Pharmaceutical Sciences, Naresuan University, Phitsanulok, Thailand 65000, Thailand

,

Kitsana Jancharoen

^bLaboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6 Road, Laksi, Bangkok, Thailand 10210, Thailand

,

Paratchata Batsomboon

^bLaboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6 Road, Laksi, Bangkok, Thailand 10210, Thailand

,

Somsak Ruchirawat

^aProgram in Chemical Sciences, Chulabhorn Graduate Institute, 906 Kamphaeng Phet 6 Road, Laksi, Bangkok, Thailand 10210, Thailand

^bLaboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6 Road, Laksi, Bangkok, Thailand 10210, Thailand

^dCenter of Excellence on Environmental Health and Toxicology, Office of the Permanent Secretary (OPS), Ministry of Higher Education, Science, Research and Innovation (MHESI), Bangkok, Thailand 10400, Thailand

,

Poonsakdi Ploypradith∗

^aProgram in Chemical Sciences, Chulabhorn Graduate Institute, 906 Kamphaeng Phet 6 Road, Laksi, Bangkok, Thailand 10210, Thailand

^bLaboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6 Road, Laksi, Bangkok, Thailand 10210, Thailand

^dCenter of Excellence on Environmental Health and Toxicology, Office of the Permanent Secretary (OPS), Ministry of Higher Education, Science, Research and Innovation (MHESI), Bangkok, Thailand 10400, Thailand

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Abstract

Starting from (E)-(2-stilbenyl/styrenyl)methanols, two distinct scaffolds, namely isochroman-4-ols and 1,3-dihydroisobenzofurans (phthalans), could be synthesized via an epoxidation/cyclization strategy. Indenes, readily accessible from the same starting materials, could undergo epoxidation/ring-opening/cyclization to provide tetrahydro-2H-indeno[2,1-b]furan-2-ones. Stilbene/styrene/indene epoxidation by m-CPBA or DMDO converted the nucleophilic olefin into the electrophilic epoxide, which subsequently underwent the regioselective ring-opening either by the hydroxy or the ester group to furnish the corresponding products with stereocontrol at the newly formed stereogenic centers. The reaction proceeded under substrate control to yield each product type exclusively.

Key words

Key words

epoxidation - cyclization - carbocation - fused-ring systems - stereoselectivity

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Supplementary Material

Supplementary Material

Supporting Information