Journal
CHEMICAL & PHARMACEUTICAL BULLETIN
Volume 64, Issue 7, Pages 961-965Publisher
PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/cpb.c16-00190
Keywords
flavanone; regioselective deprotection; lipase-catalyzed transesterification
Funding
- Ministry of Education, Culture, Sports, Science and Technology of Japan [26450143]
- Grants-in-Aid for Scientific Research [26450143] Funding Source: KAKEN
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Sakuranetin and selinone were successfully synthesized utilizing the regioselective deacetylation of naringenin triacetate. Deacetylation of the latter at C-7 with imidazole in 1,4-dioxane at 40 degrees C furnished the corresponding diacetate in 80% yield. Methylation of the obtained free hydroxy group and subsequent removal of the remaining two acetyl groups gave sakuranetin, which was previously isolated as a phytoalexin against rice blast disease fungus, Pyricularia oryzae, in 71% overall yield. The same intermediate, naringenin triacetate, was subjected to transesterification with 2-propanol in tetrahydrofuran, catalyzed by Candida antarctica lipase B. A contrasting regioselective preference for C-4' deacetylation was observed, giving an isomeric diacetate in 82% yield. Prenylation of the free hydroxy group under Mitsunobu conditions and subsequent deprotection furnished selinone, which was previously isolated from Monotes engleri and exhibits antifungal activity against Candida albicans, in 55% overall yield.
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