[Chemical equation presented] 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 c/s-α-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 irldoids.
ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry