Improved Synthesis of Dihydrothebainone and Its 14 β-Epimer

An improved synthesis for the preparation of diastereomerically pure dihydrothebainone (1) from thebaine (3) is reported. A 41% overall yield was realized over three steps via direct transformation of dihydrothebaine-Ø (4) to thebainone-A (6) with 6N HCl.

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Bibliographic Details
Published inSynthetic communications Vol. 28; no. 3; pp. 547 - 558
Main Authors Davidson, Marian R., Gregg, Brian T.
Format Journal Article
LanguageEnglish
Published NEW YORK Taylor & Francis Group 01.02.1998
Marcel Dekker Inc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CODEINE
DERIVATIVES
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Summary:An improved synthesis for the preparation of diastereomerically pure dihydrothebainone (1) from thebaine (3) is reported. A 41% overall yield was realized over three steps via direct transformation of dihydrothebaine-Ø (4) to thebainone-A (6) with 6N HCl.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397919808005110