Issue 19, 2010
From the journal:

Organic & Biomolecular Chemistry

Intramolecular cycloaddition in 6,6-spiroepoxycyclohexa-2,4-dienone: simple aromatics to (±)-Platencin†

Vishwakarma Singh,*a   Bharat Chandra Sahu,a   Varsha Bansala  and  Shaikh M. Mobinb  

* Corresponding authors

a Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400 076, India
E-mail: vks@chem.iitb.ac.in

b National Centre for Single Crystal X-ray diffraction, Indian Institute of Technology Bombay, Mumbai, India

Abstract

A formal total synthesis of platencin from a simple aromatic precursor is described. Transformation of the aromatic compound into reactive spiroepoxycyclohexa-2,4-dienone and intramolecular cycloaddition are the key features of our methodology. 2-Hydroxymethyl-6-(3-hydroxy-hex-5-enyl)-phenol was oxidized with NaIO4 to give a dimer that, upon a retro-Diels–Alder reaction, generated the spiroepoxycyclohexa-2,4-dienone that underwent intramolecular Diels–Alder reaction to give a tricyclic adduct having a core structure of platencin and appropriately disposed functional groups in a single step. Reduction of the double bond present in the ethano-bridge, manipulation of the oxirane ring and introduction of a double bond in the six-membered ring furnished a tricyclic intermediate which has already been converted into platencin.

Graphical abstract: Intramolecular cycloaddition in 6,6-spiroepoxycyclohexa-2,4-dienone: simple aromatics to (±)-Platencin

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Article information

DOI
https://doi.org/10.1039/C004316H
Article type
Paper
Submitted
17 Mar 2010
Accepted
22 Jun 2010
First published
04 Aug 2010

Org. Biomol. Chem., 2010,8, 4472-4481

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Intramolecular cycloaddition in 6,6-spiroepoxycyclohexa-2,4-dienone: simple aromatics to (±)-Platencin

V. Singh, B. C. Sahu, V. Bansal and S. M. Mobin, Org. Biomol. Chem., 2010, 8, 4472 DOI: 10.1039/C004316H

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