title: Dramatic influence of the substitution of alkylidene-5H-furan-2-ones in Diels-Alder cycloadditions with o-quinonedimethide as diene partner: en route to the CDEF polycyclic ring system of lactonamycin.
abstract: An efficient and rapid synthesis of the CDEF ring system of lactonamycinone is reported via a highly chemo- and diastereoselective intermolecular Diels-Alder cycloaddition between trans-1,2-disilyloxybenzocyclobutene and the appropriate γ-alkylidenebutenolide. The feasibility and the total chemoselectivity of the [4 + 2] cycloaddition for the construction of a spirolactone moiety via an intramolecular approach (IMDA) using both partners is also described demonstrating the versatility of the γ-alkylidenebutenolide building block.
authors.affiliation: Aix-Marseille Université, Institut des Sciences Moléculaires de Marseille iSm2, UMR 7313, avenue Escadrille Normandie Niemen, 13397 Marseille cedex 20, France.
authors.forename: Sébastien
authors.initials: S
authors.lastname: Dubois
authors.forename: Fabien
authors.initials: F
authors.lastname: Rodier
authors.forename: Romain
authors.initials: R
authors.lastname: Blanc
authors.forename: Raphaël
authors.initials: R
authors.lastname: Rahmani
authors.forename: Virginie
authors.initials: V
authors.lastname: Héran
authors.forename: Jérôme
authors.initials: J
authors.lastname: Thibonnet
authors.forename: Laurent
authors.initials: L
authors.lastname: Commeiras
authors.forename: Jean-Luc
authors.initials: JL
authors.lastname: Parrain
mesh_terms: D000478:Alkylation; D003500:Cyclization; D005663:Furans / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis; D011809:Quinones / Q000737:chemistry*; D013148:Spironolactone / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D005663:Furans; D007211:Indoles; D009285:Naphthoquinones; D011809:Quinones; C102442:lactonamycin; D013148:Spironolactone; C039281:furan