Stereoselective synthesis of morphine fragments trans- and cis-octahydro-1H-benzo[4,5]furo[3,2-e]isoquinolines |
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| Authors: | Ling-Wei Hsin Li-Te Chang Chien-Wei Chen Chia-Huei Hsu Hung-Wei Chen |
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| Affiliation: | Institute of Pharmaceutical Sciences, College of Medicine, National Taiwan University, No. 1, Section 1, Jen-Ai Road, Room 1336, Taipei 10018, Taiwan, ROC |
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| Abstract: | A stereoselective synthesis of the ACNO partial structures of morphine has been developed. Palladium-catalyzed cyclization of carbamate 2 provided the tetracyclic (ACNO) 3-ethoxycarbonyl-9-methoxy-2,3,5,6,7,7a-hexahydro-1H-benzofuro[3,2-e]isoquinoline (14); while treatment of 5-(2-bromo-6-methoxyphenoxy)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline (8) under the same reaction condition gave 8a-(2-hydroxy-3-methoxyphenyl)-1,2,3,4,6,7,8,8a-octahydroisoquinoline (11) via an unusual Claisen rearrangement. 9-Methoxy-3-methyl-2,3,5,6,7,7a-hexahydro-1H-benzofuro[3,2-e]isoquinoline (7) was successfully transformed to trans-octahydroisoquinoline 3 and cis-octahydroisoquinoline 4 via catalytical hydrogenation over PtO2 and chemical reduction with acidic NaBH4, respectively. |
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| Keywords: | Stereoselective Morphine Intramolecular cyclization Heck reaction Claisen rearrangement |
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