Oxidative Dearomatization of o-Hydroxymethylphenol and Intramolecular π4s+π2s Cycloaddition: An Expedient Synthesis of a Tricyclic Intermediate for Platencin

Vishwakarma Singh; Beauty Das; Shaikh M. Mobin

doi:10.1055/s-0033-1339196

Synlett, Table of Contents

Synlett 2013; 24(12): 1583-1587
DOI: 10.1055/s-0033-1339196

letter

Oxidative Dearomatization of o-Hydroxymethylphenol and Intramolecular π⁴s+π²s Cycloaddition: An Expedient Synthesis of a Tricyclic Intermediate for Platencin

Vishwakarma Singh*

^aDepartment of Chemistry, Indian Institute of Technology Bombay, Mumbai 400 076, India Fax: +91(22)25723480 Email: vks@chem.iitb.ac.in

,

Beauty Das

^aDepartment of Chemistry, Indian Institute of Technology Bombay, Mumbai 400 076, India Fax: +91(22)25723480 Email: vks@chem.iitb.ac.in

,

Shaikh M. Mobin

^bDiscipline of Chemistry, Indian Institute of Technology Indore, Indore 452 017, India

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Abstract

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Abstract

A synthesis of a tricyclic intermediate for platencin from a simple aromatic precursor is described. Oxidative dearomatization and intramolecular Diels–Alder reaction are key features of the approach.

Key words

oxidative dearomatization - intramolecular Diels–Alder reaction - cycloaddition - spiroepoxycyclohexa-2,4-dienone

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References and Notes

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12 Crystal Data for 13 C₁₂H₁₄O₂, M = 190.23, monoclinic, space group P2₁/n, a = 6.4692(3) Å, b = 21.7808(6) Å, c = 7.3963(3) Å, α = 90°, β = 113.217(4)°, γ = 90°, V = 957.77(6) Å³, D _c = 1.319 Mg m^–3, Z = 4, F(000) = 408, size: 0.33 × 0.26 × 0.21 mm³, wavelength = 0.71073 Å, GoF = 1.077, absorption coefficient = 0.088 mm^–1, total/unique reflections = 6555/1684 [R _int = 0.0138], T = 150(2) K, θ range = 3.53–24.99°, final R [I > 2σ(I)]: R1 = 0.0317, wR2 = 0.0791, R (all data): R1 = 0.0366, wR2 = 0.0808. Crystallographic data has been deposited with Cambridge Crystallographic data Centre, CCDC no. 925908. Copy of the data can be obtained, free of charge, on application to CCDC. E-mail. deposit@ccdc.cam.ac.uk.

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