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

Content Provider	Royal Society of Chemistry (RSC)
Author	Sahu, Bharat Chandra Bansal, Varsha Singh, Vishwakarma Mobin, Shaikh M.
Copyright Year	2010
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.
Starting Page	4472
Ending Page	4481
Page Count	10
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	8
Issue Number	19
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/c004316h
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Cycloaddition Phenol Alkene Aromaticity Retro-Diels\u2013Alder reaction Ethylene oxide Protein dimer Diels\u2013Alder reaction Total synthesis Adduct
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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