A concise, biomimetic total synthesis of (+)-davanone.
A concise, biomimetic synthesis of the antifungal and antispasmodic natural product (+)-davanone is described. The key stereoselective reactions are a Sharpless asymmetric epoxidation, a thiazolium-catalyzed esterification, and a palladium-mediated cyclization. All carbons are derived from isoprene units and no protecting groups are used, permitting an atom- and redox-economical synthesis.
Department of Chemistry, Harvey Mudd College, 301 Platt Boulevard, Claremont, California 91711, USA.
Karen C
KC
Morrison
Jonathan P
JP
Litz
Kathryn P
KP
Scherpelz
Paul D
PD
Dossa
David A
DA
Vosburg
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry; D019306:Artemisia / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D004951:Esterification; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D010276:Parasympatholytics / Q000138:chemical synthesis* / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013844:Thiazoles / Q000737:chemistry
D000935:Antifungal Agents; D001688:Biological Products; D010276:Parasympatholytics; D012717:Sesquiterpenes; D013844:Thiazoles; C520072:davanone; D010165:Palladium