Ring expansion approach for the synthesis of the (3S,4S)-hexahydroazepine core of balanol and ophiocordin |
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Authors: | J.S Yadav Ch Srinivas |
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Affiliation: | Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India |
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Abstract: | A new and efficient formal total synthesis of (3S,4S)-balanol, a potent protein kinase C inhibitor, was accomplished from tri-O-acetyl-d-glucal. Balanol and ophiocordin consists of a chiral hexahydro azepine-containing fragment and a benzophenone fragment. The azepine core was prepared in chiral form through intramolecular aza Wittig reaction. A triphenylphosphine mediated ring expansion process was employed to form the seven-membered nitrogen heterocycle. The aldehyde equivalent key intermediate was treated with triphenylphosphine to give the azepine core. To demonstrate the applicability of the new route, a synthesis of the balanol is described. |
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Keywords: | balanol ophiocordin ring expansion |
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