title: Iodine-catalyzed highly diastereoselective synthesis of trans-2,6-disubstituted-3,4-dihydropyrans: application to concise construction of C28-C37 bicyclic core of (+)-sorangicin A.
abstract: A novel iodine-catalyzed highly diastereoselective synthesis of trans-2,6-disubstituted-3,4-dihydropyrans have been achieved from delta-hydroxy alpha,beta-unsaturated aldehydes by treating with allyltrimethyl silane in THF at room temperature with good to excellent yields. This methodology has been successfully implemented for a concise asymmetric synthesis of C28-C37 dioxabicyclo[3.2.1]octane ring system of (+)-sorangicin A in 8 steps with 21% overall yield.
authors.affiliation: Organic Chemistry Division-I, Indian Institute of Chemical Technology, Council of Scientific & Industrial Research (CSIR), Habsiguda, Uppal Road, Hyderabad-500007, India. mohapatra@iict.res.in
authors.forename: Debendra K
authors.initials: DK
authors.lastname: Mohapatra
authors.forename: Pragna P
authors.initials: PP
authors.lastname: Das
authors.forename: Manas Ranjan
authors.initials: MR
authors.lastname: Pattanayak
authors.forename: J S
authors.initials: JS
authors.lastname: Yadav
mesh_terms: D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000617:Aminoglycosides; D001643:Bridged Bicyclo Compounds; D011714:Pyrans; C051799:sorangicin A; D007455:Iodine