Palladium-catalyzed potassium enoxyborate alkylation of enantiopure Hajos-Parrish indenone to construct rearranged steroid ring systems.
Here we report the stereo- and regiospecific C-6 alkylation of a trans-inden-5-one (from optically pure Hajos-Parrish ketone) with allylic electrophiles. Use of this alkylation procedure has led to an improved synthesis of the benz[f]indene ring system and the first enantiospecific total syntheses of the cyclopenta[b]anthracene and cyclopenta[b]phenanthrene ring systems (two synthetic routes).
Jastrzebska
Izabella
I
Department of Molecular Biology and Pharmacology, Washington University School of Medicine, St. Louis, Missouri 63110, USA.
Scaglione
Jamie B
JB
Dekoster
Gregory T
GT
Rath
Nigam P
NP
Covey
Douglas F
DF
D000478:Alkylation; D000873:Anthracenes / Q000737:chemistry; D001554:Benzene / Q000737:chemistry; D001881:Borates / Q000737:chemistry*; D002384:Catalysis; D007192:Indenes / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013256:Steroids / Q000737:chemistry*
D000873:Anthracenes; D001881:Borates; D007192:Indenes; D013256:Steroids; D010165:Palladium; C034020:anthracene; D001554:Benzene