title: Chemoenzymatic collective synthesis of optically active hydroxyl(methyl)tetrahydronaphthalene-based bioactive terpenoids.
abstract: Starting from succinic anhydride and 2-methylanisole, a chemoenzymatic collective formal/total synthesis of several optically active tetrahydronaphthalene based bioactive natural products has been presented via advanced level common precursors; the natural product and antipode (-)/(+)-aristelegone B. Regioselective benzylic oxidations, stereoselective introduction of hydroxyl groups at the α-position of ketone moiety in syn-orientation, efficient enzymatic resolutions with high enantiomeric purity, stereoselective reductions, samarium iodide induced deoxygenations and tandem acylation-Wittig reactions without racemization and/or eliminative aromatization were the key features. An attempted diastereoselective synthesis of (±)-vallapin has also been described.
authors.affiliation: Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India. np.argade@ncl.res.in.
authors.forename: Ramesh U
authors.initials: RU
authors.lastname: Batwal
authors.affiliation: Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India. np.argade@ncl.res.in.
authors.forename: Narshinha P
authors.initials: NP
authors.lastname: Argade
mesh_terms: D000215:Acylation; D000840:Anisoles / Q000138:chemical synthesis / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D008745:Methylation; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000840:Anisoles; D001688:Biological Products; D013729:Terpenes; D013764:Tetrahydronaphthalenes; C428434:2-methylanisole