Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2013; 24(3): 369-374
DOI: 10.1055/s-0032-1318114
DOI: 10.1055/s-0032-1318114
letter
Total Synthesis of Dihydrocodeine and Hydrocodone via a Double Claisen Rearrangement and C-10/C-11 Closure Strategy
Further Information
Publication History
Received: 06 December 2012
Accepted after revision: 04 January 2013
Publication Date:
21 January 2013 (online)


Abstract
Dihydrocodeine and hydrocodone were synthesized from bromobenzene in 16 and 17 transformations, respectively. The key steps involved the toluene dioxygenase-mediated dihydroxylation of bromobenzene by whole-cell fermentation with E. coli JM109(pDTG601A), Kazmaier–Claisen rearrangement of glycinate ester, Claisen rearrangement to set the C-13 quaternary center, and C-10–C-11 closure. Experimental procedures are provided for the key steps.