Application of a domino intramolecular enyne metathesis/cross metathesis reaction to the total synthesis of (+)-8-epi-xanthatin.
[reaction: see text] The first total synthesis of the novel sesquiterpene lactone (+)-8-epi-xanthatin (1) has been achieved starting from the commercially available ester 8. The synthesis features an asymmetric aldol reaction and palladium-catalyzed carbonylation/lactonization sequence leading to 4 and a domino ring-closing enyne metathesis/cross metathesis reaction to afford 1.
Kummer
David A
DA
Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712, USA.
Brenneman
Jehrod B
JB
Martin
Stephen F
SF
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
D000480:Alkynes; D005663:Furans; C022186:xanthatin; D010165:Palladium