Gimisis T, Kampf JW, Koreeda M.
{Synthesis of methylene-bridged polycyclic aromatic hydrocarbons: an efficient, double Friedel-Crafts cyclization approach to 11H-benz[bc]aceanthrylene}. J. Org. Chem. [Internet]. 1993;58:5858–5861.
WebsiteAbstractA five-step synthesis of 3-methylcholanthrene (1) has been achieved starting from 5-methylhomophthalic anhydride and N,N-diethyl-1-naphthamide in 55{%} overall yield. Treatment of a solution of the preformed lithium enolate of 5-methylhomophthalic anhydride (3) with an equimolar solution of 2-lithio-1-naphthamide (4), followed by acid hydrolysis, provides cleanly the spirobislactone 5 in 80{%} overall yield. In addition, the synthesis features a unique, highly selective double Friedel-Crafts cyclization of the aryl diacid 2 with PPA to give rise, after acetylation, to keto acetate 6. © 1993 America Chemical Society.
Gimisis T, Koreeda M.
{A HIGHLY EFFICIENT SYNTHESIS OF 3-METHYLCHOLANTHRENE}. J. Org. Chem. [Internet]. 1993;58:7158–7161.
WebsiteAbstractA five-step synthesis of 3-methylcholanthrene (1) has been achieved starting from 5-methylhomophthalic anhydride and N,N-diethyl-1-naphthamide in 55{%} over all yield. Treatment of a solution of the preformed lithium enolate of 5-methylhomophthalic anhydride (3) with an equimolar solution of 2-lithio-1-naphthamide (4), followed by acid hydrolysis, provides cleanly the spirobislactone 5 in 80{%} overall yield. In addition, the synthesis features a unique, highly selective double Friedel-Crafts cyclization of the aryl diacid 2 with PPA to give rise, after acetylation, to keto acetate 6.
Gopalaswamy R, Tuinman RJ, Gimisis T, Jung KY, Koreeda M.
{SYNTHESIS OF THE OPTICALLY-ACTIVE DIOL EPOXIDE METABOLITES OF CARCINOGENIC PAHS}. Abstr. Pap. Am. Chem. Soc. 1993;206:350–ORGN.
