Synthesis of 7-azabicyclo[4.3.1]decane ring system from tricarbonyl(tropone)iron via intramolecular Heck reactions

Submitting author affiliation:
Lafayette College, Easton, United States

Beilstein Arch. 2023, 202321.

Published 26 May 2023

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The 7-azabicyclo[4.3.1]decane ring system, common to a number of biologically active alkaloids, was accessed from tropone (via its η4-diene complex with Fe(CO)3) in a short sequence of steps: 1) nucleophilic amine addition and subsequent Boc-protection; 2) photochemical demetallation of the iron complex; 3) intramolecular Heck reaction. Minor modifications to the protocol enabled access to the related 2-azabicyclo[4.4.1]undecane and 8-azabicyclo[5.3.0]decane ring systems, albeit in lower yield.

Keywords: alkaloids; Heck reaction; azabicycles; tropone; iron complex

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Shoemaker, A. H.; Foker, E. A.; Uttaro, E. P.; Beitel, S. K.; Griffith, D. R. Beilstein Arch. 2023, 202321. doi:10.3762/bxiv.2023.21.v1

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