The synthesis of 2-benzazocines using ring-closing metathesis as a key step

• Published in: Tetrahedron Vol. 63; no. 22; pp. 4737 - 4747
• Main Authors: Panayides, Jenny-Lee, Pathak, Rakhi, Panagiotopoulos, Helen, Davids, Hajierah, Fernandes, Manuel A., de Koning, Charles B., van Otterlo, Willem A.L.
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 28-05-2007
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2007.03.087

A number of protected 7-isopropoxy-8-methoxy-1,2,3,6-tetrahydro-2-benzazocines were synthesized from 2-allyl-3-isopropoxy-4-methoxybenzaldehyde using ring-closing metathesis as the key step. In addition, two 9-isopropoxy-8-methoxy-3,6-dihydro-2-benzazocines were synthesized from 5-isopropoxy-4-methoxy-2-[(1
E)-3-phenyl-2-propenyl]benzaldehyde, which in turn was obtained from the thermal Claisen–Cope rearrangement of 4-methoxy-3-{[(2
E)-3-phenyl-2-propenyl]oxy}benzaldehyde. Finally, five of the 2-benzazocine compounds were tested for anti-cancer activity.
[Display omitted] A number of substituted 2-benzazocines were synthesized from 2-allyl-3-isopropoxy-4-methoxybenzaldehyde and 5-isopropoxy-4-methoxy-2-[(1
E)-3-phenyl-2-propenyl]benzaldehyde using ring-closing metathesis as the key step.