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A facile synthesis of (6S,1′S)-(+)-hernandulcin and (6S,1′R)-(+)-epihernandulcin

✍ Scribed by Jung Hun Kim; Hyun Jin Lim; Seung Hoon Cheon

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
176 KB
Volume
59
Category
Article
ISSN
0040-4020

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✦ Synopsis

A facile total synthesis of (þ)-hernandulcin (1) was accomplished from (2)-isopulegol in 6 steps with 15% overall yield. Epoxidation of (2)-isopulegol with m-chloroperbenzoic acid followed by opening of the epoxide 3a with prenyl Grignard afforded the tertiary alcohol 4a with correct C-6 and C-1 0 stereochemistry as a major product. Oxidation of the secondary alcohol in compound 4a to the ketone 5a was accomplished in high yield by using TPAP and N-methylmorpholine N-oxide. Conversion of the ketone 5a to a,b-unsaturated ketone via organoselenium intermediate gave (þ)-hernandulcin (1). This method was also successfully applied to the synthesis of (þ)-epihernandulcin (2).

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