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Synlett 2013; 24(12): 1583-1587
DOI: 10.1055/s-0033-1339196
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
Weitere Informationen
Publikationsverlauf
Received: 29. März 2013
Accepted after revision: 20. Mai 2013
Publikationsdatum:
20. Juni 2013 (online)
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-dienoneSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
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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.