Synthetic approaches to nortropanes and nortrop-6-enes; intramolecular displacement by nitrogen in 7-membered rings

A Naylor, N Howarth, JR Malpass

Index: Naylor, Antoinette; Howarth, Nicola; Malpass, John R. Tetrahedron, 1993 , vol. 49, # 2 p. 451 - 468

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Citation Number: 22

Abstract

Abstract The synthesis of simple nortropane and nortropd-ene derivatives from cyclohepta-1, 3-diene is described. The key intermediates are trans-I-amino4chlorocycloheptanes and- cyclohept-2-enes which are derived efficiently from the corresponding cis-amino-alcohols and undergo intramolecular cyclisation. Corresponding derivatisation of cyclohexa-and cycloocta-1, 3-dienes is explored and attempts to achieve Pd-catalysed cyclisation of I- ...