title: A chemoenzymatic synthesis of hept-6-ene-2,5-diol stereomers: application to asymmetric synthesis of decarestrictine L, pyrenophorol, and stagonolide E.
abstract: The stereomers of hept-6-ene-2,5-diol derivatives were conceived as useful chiral intermediates and were synthesized starting from sulcatol using two lipase-catalyzed acylation reactions as the key steps. The versatility of the intermediates was demonstrated by converting them to the titled tetrahydropyran, macrolide, and macrodiolide compounds using standard synthetic protocols.
authors.affiliation: Bio-Organic Division, Bhabha Atomic Research Centre , Mumbai 400 085, India.
authors.forename: Sucheta
authors.initials: S
authors.lastname: Chatterjee
authors.forename: Sneha
authors.initials: S
authors.lastname: Ghadigaonkar
authors.forename: Payel
authors.initials: P
authors.lastname: Sur
authors.forename: Anubha
authors.initials: A
authors.lastname: Sharma
authors.forename: Subrata
authors.initials: S
authors.lastname: Chattopadhyay
mesh_terms: D000215:Acylation; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008049:Lipase / Q000737:chemistry* / Q000378:metabolism; D018942:Macrolides / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006571:Heterocyclic Compounds; D006573:Heterocyclic Compounds, 1-Ring; D007659:Ketones; D007783:Lactones; D018942:Macrolides; D011714:Pyrans; C000599834:decarestrictine L; C509954:pyrenophorol; C527511:stagonolide; D008049:Lipase