An oxidative entry into the amido trioxadecalin ring system.
The amido trioxadecalin ring system is a key structural component of the architecturally interesting anticancer and immunosuppressive agents of the mycalamide, theopederin, and onnamide families of natural products. We report a new entry into this structure in which a mixed acetal serves as a surrogate for a formaldehyde hemiacetal in an addition to an oxidatively generated acyliminium ion. The stereochemical outcome of this process can be explained by the conformational preferences of the product ring system. [reaction: see text]
Rech
Jason C
JC
Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.
Floreancig
Paul E
PE
D000080:Acetals / Q000737:chemistry; D000577:Amides / Q000138:chemical synthesis*; D003500:Cyclization; D008387:Marine Toxins / Q000138:chemical synthesis; D009281:Naphthalenes / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D011714:Pyrans / Q000737:chemistry; D013237:Stereoisomerism
D000080:Acetals; D000577:Amides; D008387:Marine Toxins; D009281:Naphthalenes; D011714:Pyrans; C449320:oxadecalin