title: Synthesis of the macrolactone core of (+)-neopeltolide by transannular cyclization.
abstract: The synthesis of the macrolactone core of (+)-neopeltolide has been achieved. The key synthetic strategy involves the highly diastereoselective synthesis of the 2,6-cis-disubstituted tetrahydropyran ring by a transannular cyclization of δ-hydroxy alkene using mercuric trifluoroacetate. Two of the six stereocenters C-5 and C-11 were realized from L-malic acid, while the remaining stereocenters C-3 (Sharpless asymmetric epoxidation), C-7 (transannular cyclization), C-9 (regioselective epoxide opening) and C-13 (chelation controlled reduction) were derived by asymmetric synthesis. The macrolactone ring was synthesized by macrocyclization using a RCM protocol.
authors.affiliation: Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad, India. esmvee@iict.res.in
authors.forename: Gangavaram V M
authors.initials: GV
authors.lastname: Sharma
authors.forename: Sheri Venkat
authors.initials: SV
authors.lastname: Reddy
authors.forename: Kallaganti V S
authors.initials: KV
authors.lastname: Ramakrishna
mesh_terms: D003500:Cyclization; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D018942:Macrolides; C519136:neopeltolide