A biomimetic approach to C-nor-D-homo-steroids.
A biomimetic three-step transformation of classical "6-6-6-5"-steroids into their C-nor-D-homo-counterparts gives an easy and fast access to this highly important substructure of natural products, as it is found in cyclopamine, and nakiterpiosin. A novel reagent combination allows for the rearrangement even of 17-keto steroids with high endoselectivity. In several examples the broadness of this strategy is outlined.
Heretsch
Philipp
P
Institut für Organische Chemie, Fakultät für Chemie und Mineralogie, Universität Leipzig, Johannisallee 29, D-04103 Leipzig, Germany.
Rabe
Sebastian
S
Giannis
Athanassios
A
D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D032701:Biomimetics / Q000379:methods*; D006718:Homosteroids / Q000138:chemical synthesis* / Q000737:chemistry; D007700:Kinetics; D013379:Substrate Specificity
D001688:Biological Products; D006718:Homosteroids