title: A facile and efficient synthesis of 4-hydroxy-2,6-cis-tetrahydropyrans via tandem cross-metathesis/thermal S(N)2' reaction: protecting-group-free synthesis of (+/-)-diospongin A.
abstract: The tandem cross-metathesis/thermal S(N)2' reaction was explored for the facile and efficient synthesis of 4-hydroxy-2,6-cis-tetrahydropyrans. The mildness of the thermal conditions allowed for the synthesis of 4-hydroxy-2,6-cis-tetrahydropyrans from base-sensitive substrates without the use of protecting groups. The tandem reaction enabled a protecting-group-free synthesis of (+/-)-diospongin A.
authors.affiliation: Department of Chemistry, Duke University, Durham, North Carolina 27708, USA.
authors.forename: Kiyoun
authors.initials: K
authors.lastname: Lee
authors.forename: Hyoungsu
authors.initials: H
authors.lastname: Kim
authors.forename: Jiyong
authors.initials: J
authors.lastname: Hong
mesh_terms: D008968:Molecular Conformation; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
chemical_list: C546294:4-hydroxy-2,6-cis-tetrahydropyran; D011714:Pyrans; C521317:diospongin A