A practical asymmetric synthesis of trans-4,5-benzhydrindan-1-ones as a precursor of A-nor B-aromatic steroidal compounds.
The enantio-controlled synthesis of trans-4,5-benzhydrindan-1-ones was achieved by means of a stereoselective [4+2] cycloaddition of o-quinodimethanes generated by a thermal cleavage of benzocyclobutene derivatives as a key step. The chiral substrates of the thermal reaction were synthesized by a diastereoselective Grignard addition to the chiral O-isopropylideneglyceroketones connected to a benzocyclobutene ring, which were simply prepared from D-mannitol as a chiral source. This approach can provide a new efficient access to A-nor B-aromatic steroidal compounds.
Matsuya
Yuji
Y
Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama 930-0194, Japan.
Masuda
Seiji
S
Itoh
Takakatsu
T
Murai
Taiki
T
Nemoto
Hideo
H
D001555:Benzene Derivatives / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013256:Steroids / Q000737:chemistry*
D001555:Benzene Derivatives; D013256:Steroids