Alpha-conidendrin as a source for preparation of sikkimotoxin derivatives.
Oxidation of alpha-conidendrin (3) by Fremy's salt favored formation of an o-quinone (4) at the pendant aromatic ring as opposed to the fused aromatic ring. Quinone reduction and phenolic methylation, followed by lactone reduction, and subsequent oxidation by dichlorodicyanoquinone produced sikkimotoxin oxabicyclooctane (7), while oxidation with cupric sulfate/potassium persulfate gave sikkimotoxin dioxatricyclodecane (8).
LaLonde
Robert T
RT
Department of Chemistry, State University of New York, College of Environmental Science and Forestry (SUNY-ESF), Syracuse, New York 13210-2726, USA. rtlalonde@syr.edu
Zhang
Mianji
M
D002384:Catalysis; D007202:Indicators and Reagents; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry*; D010084:Oxidation-Reduction; D011034:Podophyllotoxin / Q000138:chemical synthesis / Q000737:chemistry; D011809:Quinones / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis* / Q000737:chemistry*
D007202:Indicators and Reagents; D017705:Lignans; D011809:Quinones; D013764:Tetrahydronaphthalenes; C421915:conidendrin; D011034:Podophyllotoxin; C486255:sikkimotoxin