Jump to main content
Jump to site search

Issue 19, 2010
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 17 Mar 2010, accepted on 22 Jun 2010 and first published on 04 Aug 2010


Article type: Paper
DOI: 10.1039/C004316H
Citation: Org. Biomol. Chem., 2010,8, 4472-4481
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements