title: An efficient, modular approach for the synthesis of (+)-strictifolione and a related natural product.
abstract: An efficient, library amenable, "pot economical" total synthesis of (+)-strictifolione and the related natural product, (6R)-6[(E,4R,6R)-4,6-dihydroxy-10-phenyl-1-decenyl]-5,6-dihydro-2H-2-pyrone, are reported. This modular approach takes advantage of two consecutive phosphate tether-mediated, one-pot, sequential protocols, followed by a final cross metathesis to deliver both antifungal natural products in a three-pot process from the respective enantiomeric (R,R)- and (S,S)-trienes with minimal purification. A salient feature of this route is that additional protecting groups are not required as a result of the orthogonal protecting- and leaving-group properties innate to phosphate triesters.
authors.affiliation: Department of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, United States.
authors.forename: Susanthi
authors.initials: S
authors.lastname: Jayasinghe
authors.forename: Phanindra K M
authors.initials: PK
authors.lastname: Venukadasula
authors.forename: Paul R
authors.initials: PR
authors.lastname: Hanson
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D011753:Pyrones; C476921:strictifolione