Journal
JOURNAL OF NATURAL PRODUCTS
Volume 82, Issue 1, Pages 59-65Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.8b00573
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Funding
- National Science Centre, Poland [2015/17/B/ST5/02892]
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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.
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