Volume 24, Issue 14
Natural Products
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ChemInform Abstract: Convergent Synthesis of (.+-.)-Dihydroisocodeine in 11 Steps by the Tandem Radical Cyclization Strategy. A Formal Total Synthesis of (.+-.) -Morphine.

K. A. PARKER

K. A. PARKER

Dep. Chem., Brown Univ., Providence, RI 02912, USA

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D. FOKAS

D. FOKAS

Dep. Chem., Brown Univ., Providence, RI 02912, USA

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First published: April 6, 1993

Abstract

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ChemInform Abstract

The synthesis of (.+-.)-dihydroisocodeine (VII), a precursor of morphine (VIII), proceeds via tandem cyclization of the aryl ether (IV) to give the tetracyclic styrene (V). The final bond connection is achieved by desulfonation of (V) which results in an unprecedented cyclization to afford the morphine ring system (VI) directly.

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