溝呂木―Heck 反応を基盤とする Allyl β-D-glucopyranosideからCinnamyl β-D-glucopyranoside系天然物の合成

抄録

Rhodiola rosea (Golden root) is widely distributed at high attitude in Arctic regions, and it is a popular plant for a reputation for stimulating the nervous system, decreasing depression. Cinnamyl b-D-Glucopyranosides, such as Rosin (cinnamyl O-β-D-glucopyranoside; 1) and Rosavin (cinnamyl 6-O-(β-L-arabinopyranosyl)-β-D-glucopyranoside; 6) were isolated from Rhodiola rosea as one of the major active ingredients. We have developed the simple synthesis of cinnamyl β-D-glucopyranoside analogues using palladium(II)-catalyzed Mizoroki-Heck type reaction between allyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (12) and phenylboronic acid congeners. By applying this strategy, we have achieved the synthesis of fourteen Rosin analogues (1-5, 26-34) including five natural products and three natural Rosavin analogues (6-8).

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