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Synthesis of morphine fragments spiro[benzofuran-3(2H),4′-piperidine] and octahydro-1H-benzofuro[3,2-e]isoquinoline by intramolecular Heck reaction

✍ Scribed by Chen-Yu Cheng; Jing-Ping Liou; Mei-Jing Lee

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 209 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)00976-3

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✦ Synopsis

As a better alternative to radical cyclization, 5-(2-bromo-6-methoxyphenoxy)-2-methyl-l,2,3,4,5,6,7,8-octahydroisoquinoline (2) and its 1-oxo analog 3 underwent Pdcatalyzed intramolecular cyclization to give the tetracyclic (ACNO) morphine fragments 5 and 6 respectively. 4-[(2'-Iodo-6'-methoxyphenoxy)methyl]-l-ethoxycarbonyl-l,2,5,6,tetrahydropyridine (11) reacted similarly to provide the tricyclic ANO fragment 12 in 70% yield and 45% e.e. when a Pd-(S)-BINAP complex was used as the catalyst.

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