The first enantioselective synthesis of 9-deoxygelsemide, belonging to a rare group of iridoids isolated from Gelsemium plants, is described. The key synthetic steps are a variant of the Woodward-Prevost reaction to install the characteristic cis-r-1,2-dioxygenated system at C-6 and C-7 with complete diastereoselectivity. Construction of the dihydropyran ring was achieved via formylation of lactone I, followed by dehydration of the corresponding lactol. The synthesis allowed assignment of absolute configuration to 9-deoxygelsemide and related iridoids.
Synthesis and Assignement of Absolute Configuration of the Iridoid 9-Deoxygelsemide.
PORTA, ALESSIO;ZANONI, GIUSEPPEConceptualization
;VIDARI, GIOVANNI
2010-01-01
Abstract
The first enantioselective synthesis of 9-deoxygelsemide, belonging to a rare group of iridoids isolated from Gelsemium plants, is described. The key synthetic steps are a variant of the Woodward-Prevost reaction to install the characteristic cis-r-1,2-dioxygenated system at C-6 and C-7 with complete diastereoselectivity. Construction of the dihydropyran ring was achieved via formylation of lactone I, followed by dehydration of the corresponding lactol. The synthesis allowed assignment of absolute configuration to 9-deoxygelsemide and related iridoids.File in questo prodotto:
Non ci sono file associati a questo prodotto.
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
