title: Total synthesis and determination of the absolute configuration of 5,6-dihydro-α-pyrone natural product synargentolide B.
abstract: Enantiospecific total synthesis and determination of the absolute stereochemistry of the α-pyrone-containing natural product synargentolide B were accomplished. The absolute stereochemistry of the natural product was established by synthesizing the possible diastereomers and comparison of the data with those reported for the natural product. During the process, total synthesis of the putative structure of related natural product 6R-[1S,2R,5R,6S-(tetraacetyloxy)-3E-heptenyl]-5,6-dihydro-2H-pyran-2-one was also accomplished and confirmed by X-ray crystal structure analysis. Wittig-Horner reaction of a chiral phosphonate derived from (S)-lactic acid and ring-closing metathesis were the key reactions during the course of the total synthesis.
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India. prasad@orgchem.iisc.ernet.in
authors.forename: Kavirayani R
authors.initials: KR
authors.lastname: Prasad
authors.forename: Phaneendra
authors.initials: P
authors.lastname: Gutala
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; C583527:synargentolide B