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Updated: May 27, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
(1S*,3S*,8S*,10S*)-10-Fluoro-15-oxa-tetra-cyclo-[6.6.1.0.0]penta-deca-5,12-dien-3-ol
1Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, Karnataka, India.
Abstract:
The title compound, C(14)H(17)FO(2), was obtained from anti-4a,9a:8a,10a-diep-oxy-1,4,4a,5,8,8a,9,9a,10,10a-deca-hydro-anthra-cene via tandem hydrogen-fluoride-mediated epoxide ring-opening and transannular oxacyclization. With the two cyclo-hexene rings folded towards the oxygen bridge, the title tetra-cyclic fluoro-alcohol mol-ecule displays a conformation remin-iscent of a pagoda. The crystal packing is effected via inter-molecular O-H⋯O hydrogen bonds, which link the mol-ecules into a zigzag chain along the b axis.
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