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Hydroxymethylation of protoberberine alkaloids by photoinduced SET. The total synthesis of (±)-solidaline

✍ Scribed by Rafael Suau; Francisco Nájera; Rodrigo Rico

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
643 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

The direct insertion of a hydroxymethyl group at position C-8 in a protoberberinium ion by photoaddition of methanol was approached via two mechanistic pathways: acetone-sensitized and single-electron transfer. The latter produces 8-hydroxymethylberbines in good yields after reduction, By combining this photochemical reaction with the oxidation of the photoproduct, syntheses of (+)-solidaline and its C-13 epimer from palmatine chloride were accomplished for the first time. On the other hand, insertion of a hydroxymethyl group at position 14 of the berberine skeleton in order to open a synthetic pathway for zijinlongine proved unsuccessful.

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