A concise synthesis of the tricyclic skeleton of pleuromutilin and a new approach to cycloheptenes.
[reaction: see text] A short synthesis of the tricyclic skeleton of pleuromutilin is reported, featuring an unusually efficient 8-endo-trig radical cyclization of a xanthate precursor. In the course of this study, a one-carbon ring expansion leading to cycloheptenes was uncovered.
Bacqué
Eric
E
Laboratoire de Synthèse Organique associé au CNRS, Ecole Polytechnique, 91 128 Palaiseau Cedex, France.
Pautrat
François
F
Zard
Samir Z
SZ
D003508:Cycloheptanes / Q000138:chemical synthesis* / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D011083:Polycyclic Compounds; D000097567:Pleuromutilins
D003508:Cycloheptanes; D004224:Diterpenes; D011083:Polycyclic Compounds; D000097567:Pleuromutilins