Synthesis and tautomerism of 9-azabicyclo [4.2. l] nonan-1-ols (Norhomotropan-1-ols), N-alkyl and 7, 8-dehydro-derivatives, and oxabicyclic analogues

CR Smith, DE Justice, JR Malpass

Index: Smith, Craig R.; Justice, David E.; Malpass, John R. Tetrahedron, 1994 , vol. 50, # 37 p. 11039 - 11056

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Citation Number: 15

Abstract

9-Methyl-9-azabicyclo [4.2. I] nonan-1-ol (homotropan-1-ol; homophysoperuvine) and-non-7- en-1-ol (homotrop-7-en-1-ol) have been synthesised together with the nor-systems and N- benzyl derivatives. The bicyclic amino-alcohols are shown to be in tautomeric equilibrium with the corresponding 4-aminocyclooctanones and-oct-2-enones; similar behaviour is also observed in oxabicyclic analogues. A rearrangement during attempted deprotection of the ...