Enantioselective synthesis of the ent-lomaiviticin A bicyclic core.
The bicyclic core of ent-lomaiviticin A was prepared in 11 operations from (S)-1-phenyl-2-propyn-1-ol in a two-directional route that features (1) a double Ireland Claisen rearrangement and (2) a double olefin metathesis reaction to form the key C-C bonds of the target.
Chemistry Department, The Pennsylvania State University, University Park, Pennsylvania 16802, USA. ksf@chem.psu.edu
Ken S
KS
Feldman
Brandon R
BR
Selfridge
D000475:Alkenes / Q000737:chemistry; D005449:Fluorenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D000095602:Angucyclines and Angucyclinones
D000475:Alkenes; D005449:Fluorenes; C433842:lomaiviticin A; D000095602:Angucyclines and Angucyclinones; C433843:lomaiviticin B