THE BASE-CATALYZED CYCLIZATION OF 10-OXOCITRAL. SYNTHESIS OF CHRYSOMELIDIAL AND DEHYDROIRIDODIAL

DOI: 10.1016/S0040-4039(00)84024-1

Source and publish data:

Tetrahedron Letters p. 381 - 382 (1986)

Update date:2022-08-02

Topics:

Authors:

Bellesia, Franco

Ghelfi, Franco

Pagnoni, Ugo M.

Pinetti, Adriano

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Article abstract of DOI:10.1016/S0040-4039(00)84024-1

Base treatment of 10-oxocitral (1) gives chrysomelidial (9) and dehydroiridodial (10), supporting the intermediacy of 1 in the biosynthesis of some iridoid glucosides.Cannizzaro reaction of 9 and 10 affords regioselectively a new iridolactone, 1,2-dehydroisoiridomirmecin (13).

Full text of DOI:10.1016/S0040-4039(00)84024-1

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