title: Synthesis of dihydroplakortin, 6-epi-dihydroplakortin, and their C10-desethyl analogues.
abstract: The first synthesis of the marine endoperoxide 9,10-dihydroplakortin, of its C10-desethyl analogue, and of their corresponding C6 epimers is described. Stereogenic centers at C4 and at the lateral chain have been stereoselectively synthesized through Evans' chiral auxiliary chemistry. Moreover, the reported synthesis features a one-pot three-step hydroperoxysilylation/cyclization reaction for the construction of the endoperoxide ring system. Homologation of the aldehyde resulting from diol cleavage through a Wittig-based strategy gave access to the ester-containing lateral chain at C3.
authors.affiliation: Dipartimento Farmaco Chimico Tecnologico (DFCT), University of Siena, via Aldo Moro 2, 53100 Siena, Italy.
authors.forename: Sandra
authors.initials: S
authors.lastname: Gemma
authors.forename: Emanuele
authors.initials: E
authors.lastname: Gabellieri
authors.forename: Salvatore
authors.initials: S
authors.lastname: Sanna Coccone
authors.forename: Francesc
authors.initials: F
authors.lastname: Martí
authors.forename: Orazio
authors.initials: O
authors.lastname: Taglialatela-Scafati
authors.forename: Ettore
authors.initials: E
authors.lastname: Novellino
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Campiani
authors.forename: Stefania
authors.initials: S
authors.lastname: Butini
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008387:Marine Toxins / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010545:Peroxides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C550068:6-epi-dihydroplakortin; D000447:Aldehydes; D004852:Epoxy Compounds; D008387:Marine Toxins; D010545:Peroxides