Vinylogous addition of siloxyfurans to benzopyryliums: a concise approach to the tetrahydroxanthone natural products.
A concise approach to the tetrahydroxanthone natural products employing vinylogous addition of siloxyfurans to benzopyryliums and a late-stage Dieckmann cyclization has been developed. With this methodology, chiral, racemic forms of the natural products blennolides B and blennolide C have been synthesized in a maximum of four steps from a 5-hydroxychromone substrate. The regio- and diastereoselectivity of the vinylogous additions was probed using computational studies, which suggested the involvement of Diels-Alder-like transition states.
Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, Boston, Massachusetts 02215, United States.
Tian
T
Qin
Richard P
RP
Johnson
John A
JA
Porco
D001688:Biological Products / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D011714:Pyrans / Q000737:chemistry*; D044004:Xanthones / Q000737:chemistry*
D001688:Biological Products; D005663:Furans; D011714:Pyrans; D044004:Xanthones
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