Computationally guided organometallic chemistry: preparation of the heptacyclic pyrazine core of ritterazine N.
Diels-Alder cycloaddition of 10 followed by Wittig homologation and intramolecular diene cyclozirconation of the resulting triene under equilibrating conditions led to the tricyclic 6-6-5 ketone 5 with high diastereocontrol. The derived alpha-azido ketone 16 cyclized efficiently to the heptacyclic pyrazine core of ritterazine N.
Taber
Douglass F
DF
Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, USA. taberdf@udel.edu
Taluskie
Karen V
KV
D003198:Computer Simulation; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D011719:Pyrazines / Q000138:chemical synthesis / Q000737:chemistry*; D013141:Spiro Compounds; D013237:Stereoisomerism; D013256:Steroids; D015040:Zirconium / Q000737:chemistry*
D006576:Heterocyclic Compounds, 4 or More Rings; D009942:Organometallic Compounds; D011719:Pyrazines; D013141:Spiro Compounds; D013256:Steroids; C516092:ritterazine N; D015040:Zirconium