Stereochemically general approach to adjacent bis(tetrahydrofuran) cores of annonaceous acetogenins.
A series of six 2,5-disubstituted adjacent bis(tetrahydrofuran) stereoisomers with trans/erythro/cis, trans/threo/trans, or cis/threo/cis relative stereochemistry have been synthesized from known dihydroxycyclooctenes via ring opening/cross metathesis and Pd(0)-mediated asymmetric double cycloetherification. The stereochemistry of four of these isomers has been found in the biologically active annonaceous acetogenin natural products. [reaction: see text].
Wysocki
Laura M
LM
Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, USA.
Dodge
Matthew W
MW
Voight
Eric A
EA
Burke
Steven D
SD
D054378:Acetogenins; D029061:Annonaceae / Q000737:chemistry*; D003500:Cyclization; D004146:Dioxanes / Q000737:chemistry; D004987:Ethers / Q000138:chemical synthesis; D005233:Fatty Alcohols / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D010165:Palladium / Q000737:chemistry; D012997:Solvents; D013237:Stereoisomerism
D054378:Acetogenins; D004146:Dioxanes; D004987:Ethers; D005233:Fatty Alcohols; D005663:Furans; D007783:Lactones; D012997:Solvents; C018674:tetrahydrofuran; D010165:Palladium