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Updated: Feb 14, 2026

Synthesis of Single-Crystalline Core-Shell Metal-Organic Frameworks
Published on: February 10, 2023
A practical synthesis of (+/-)-alpha-isosparteine from a tetraoxobispidine core
Paul R Blakemore1, Colin Kilner, Neil R Norcross
1Department of Chemistry, Oregon State University, Corvallis, Oregon 97331-4003, USA. paul.blakemore@science.oregonstate.edu
Abstract:
[reaction: see text] The title alkaloid was synthesized in racemic form from 3,7-diallyl-2,4,6,8-tetraoxo-3,7-diazabicyclo[3.3.1]nonane (7) by a regioselective diallylation reaction followed by double ring-closing olefin metathesis and exhaustive reduction. Tetraoxobispidine 7 was itself prepared in three simple operations from dimethyl malonate. The entire sequence to alpha-isosparteine was conducted on a multigram scale and proceeded without recourse to chromatography.
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