Revision of the Structure of N,O‑Diacetylsolasodine. Unusual Epimerization at the Spiro Carbon Atom during Acetylation of Solasodine

Revision of the Structure of N,O‑Diacetylsolasodine. Unusual Epimerization at the Spiro Carbon Atom during Acetylation of Solasodine

The steroidal alkaloid solasodine (1) undergoes inversion of configuration at the C-22 spiro atom when treated with acetic anhydride–pyridine at ambient temperature. The basic solvolysis of the N,O-diacetyl derivative (2) reverses the reaction, yielding the starting solasodine (1). The mechanisms of...

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Veröffentlicht in:Journal of natural products (Washington, D.C.) D.C.), 2019-01, Vol.82 (1), p.59-65
Hauptverfasser: Czajkowska-Szczykowska, Dorota, Jastrzebska, Izabella, Rode, Joanna E, Morzycki, Jacek W
Format: Artikel
Sprache:eng
Schlagworte:
Acetylation
Solanaceous Alkaloids - chemistry
Stereoisomerism
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Zusammenfassung:The steroidal alkaloid solasodine (1) undergoes inversion of configuration at the C-22 spiro atom when treated with acetic anhydride–pyridine at ambient temperature. The basic solvolysis of the N,O-diacetyl derivative (2) reverses the reaction, yielding the starting solasodine (1). The mechanisms of both processes (acetylation and deacetylation) were studied in terms of possible reaction pathways.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.8b00573