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Synfacts 2010(2): 0131-0131
DOI: 10.1055/s-0029-1219022
DOI: 10.1055/s-0029-1219022
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Alkaloid (±)-G. B. 13
Contributor(s):Philip KocienskiK. K. Larson, R. Sarpong*
University of California, Berkeley, USA
Total Synthesis of Alkaloid (±)-G. B. 13 Using a Rh(I)-Catalyzed Ketone Hydroarylation and Late-Stage Pyridine Reduction
J. Am. Chem. Soc. 2009, 131: 13244-13245
University of California, Berkeley, USA
Total Synthesis of Alkaloid (±)-G. B. 13 Using a Rh(I)-Catalyzed Ketone Hydroarylation and Late-Stage Pyridine Reduction
J. Am. Chem. Soc. 2009, 131: 13244-13245
Further Information
Publication History
Publication Date:
21 January 2010 (online)
Key words
alkaloid G. B. 13 - allylic transposition - hydroarylation - rhodium - palladium
Significance
G. B. 13 is one of the 28 Galbulimima alkaloids isolated from a tree in Papua New Guinea. Some members of the family (e.g. himbacine) have potentially useful biological activity. The key step in the synthesis depicted is an unprecedented intramolecular rhodium(I)-catalyzed hydroarylation reaction (H → I).
Comment
A vexatious step was the 1,3-allylic transposition of the alcohol C. A variety of reagents and conditions offered little hope until the discovery that the Parikh-Doering conditions were effective.