Concise syntheses of the natural products (+)-sylvaticin and (+)-cis-sylvaticin.
Two concise syntheses of the natural products cis-sylvaticin and sylvaticin are reported, using oxidative cyclization methodology as the key step. A sequential solvolysis/hydride shift/intramolecular reduction cascade was used to establish the trans stereochemistry of one of the THF rings of sylvaticin.
Donohoe
Timothy J
TJ
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. timothy.donohoe@chem.ox.ac.uk
Harris
Robert M
RM
Williams
Oliver
O
Hargaden
Gráinne C
GC
Burrows
Jeremy
J
Parker
Jeremy
J
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D006900:Hydroxylation; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000475:Alkenes; D001688:Biological Products; D005663:Furans; C063434:sylvaticin; C004511:butenolide; D015107:4-Butyrolactone