Stereoselective total synthesis of dihydrocorynantheol.
[reaction: see text] A stereoselective synthesis of the indole alkaloid dihydrocorynantheol (1) from indole-3-acetic acid has been achieved by a sequence involving 9 as a key intermediate. The synthesis of the unsaturated lactam ring in 9 highlights a series of catalytic organometallic reactions featuring two ring-closing metatheses and a zirconocene-catalyzed carbomagnesation. Since no protecting groups were used, the present synthesis of 1 is exceedingly concise, consisting of only eight distinct operations.
Deiters
Alexander
A
Department of Chemistry and Biochemistry, The University of Texas, Austin 78712, USA.
Martin
Stephen F
SF
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
D000470:Alkaloids; C007398:dihydrocorynantheol