6533b86efe1ef96bd12cbc4e

RESEARCH PRODUCT

Enantioselective synthesis and absolute configurations of aculeatins A, B, D, and 6-epi-aculeatin D

Juan Alberto MarcoMiguel CardaEva FalomirPaula Alvarez‐bercedo

subject

Enantiopure drugAldol reactionStereochemistryChemistryOrganic ChemistryDrug DiscoveryEnantioselective synthesisAbsolute configurationStereoselectivityChirality (chemistry)6-epi-aculeatin DBiochemistry

description

The three naturally occurring, bioactive spiroacetals aculeatins A, B, and D, as well as the non-natural 6-epi-aculeatin D have been synthesized for the first time in enantiopure form using an asymmetric allylation as the only chirality source. A further key step was a stereoselective aldol reaction with remote induction. The absolute configurations of the natural products have been established and an erroneous structural assignment has been corrected.

yearjournalcountryeditionlanguage
2006-10-01Tetrahedron
https://doi.org/10.1016/j.tet.2006.07.076