TY - JOUR
T1 - Synthesis of (5.R,10S,11R)-( + )-10,11-Dihydro-5-methyl-5H-dibenzo[a,d]cyclohepten-5,10-imin-11-ol
T2 - A Hydroxylated Metabolite of MK-0801
AU - Larsen, Robert D.
AU - Davis, Paul
AU - Corley, Edward G.
AU - Reider, Paul J.
AU - Lamanec, Theresa R.
AU - Grabowski, Edward J.J.
PY - 1990/1
Y1 - 1990/1
N2 - Two approaches to the synthesis of the MK-0801 metabolite, (5R,10S,11R)-(+)-10,11-dihydro-5-methyl-5H-dibenzo[a,d]cyclohepten-5,10-imin-11-ol (1a), from dibenzosuberenone (2) are presented. Selective ring opening of an aziridine with acetyl bromide and inversion of the stereochemistry provide la. Alternatively, formation of an oxazolidinone ring at the 10,11-position of the suberenone via a bromohydrin (9) is followed by acid-catalyzed cyclization of the oxazolidinone-carbinol 12 to provide la. A practical resolution for obtaining the active 5R,1OS,11R-(+) enantiomer is described.
AB - Two approaches to the synthesis of the MK-0801 metabolite, (5R,10S,11R)-(+)-10,11-dihydro-5-methyl-5H-dibenzo[a,d]cyclohepten-5,10-imin-11-ol (1a), from dibenzosuberenone (2) are presented. Selective ring opening of an aziridine with acetyl bromide and inversion of the stereochemistry provide la. Alternatively, formation of an oxazolidinone ring at the 10,11-position of the suberenone via a bromohydrin (9) is followed by acid-catalyzed cyclization of the oxazolidinone-carbinol 12 to provide la. A practical resolution for obtaining the active 5R,1OS,11R-(+) enantiomer is described.
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U2 - 10.1021/jo00288a050
DO - 10.1021/jo00288a050
M3 - Article
AN - SCOPUS:0025252313
SN - 0022-3263
VL - 55
SP - 299
EP - 304
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 1
ER -