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Hydroxymethylation of protoberberine alkaloids by photoinduced SET. The total synthesis of (±)-solidaline by Rafael Suau; Francisco Nájera; Rodrigo Rico is a Chemistry article available to read on EtoBox.

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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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Author

Rafael Suau; Francisco Nájera; Rodrigo Rico

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

1999

Language

EN

Field

Chemistry (Physical Sciences)