Total synthesis of (+)-cis-sylvaticin: double oxidative cyclization reactions catalyzed by osmium.
The double oxidative cyclization of dienes is a viable procedure for making complex natural products containing cis-THF units. A double deprotection/double oxidative cyclization strategy using catalytic osmium tetroxide was used to construct the bisheterocyclic core of cis-sylvaticin and ultimately confirm its structure. The natural product was then prepared by a short sequence of reactions that is exceptionally concise: the final route being just 13 linear steps and 19 chemical operations in total.
Donohoe
Timothy J
TJ
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, UK. timothy.donohoe@chem.ox.ac.uk
Harris
Robert M
RM
Burrows
Jeremy
J
Parker
Jeremy
J
D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009992:Osmium / Q000737:chemistry*; D010084:Oxidation-Reduction; D018515:Plant Leaves / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry*; D031045:Rollinia / Q000737:chemistry*; D013237:Stereoisomerism
D005663:Furans; C063434:sylvaticin; D009992:Osmium