title: Formal total synthesis of spirangien A.
abstract: A formal total synthesis of the spiroketal containing cytotoxic myxobacteria metabolite spirangien A (1) is described. The approach utilizes a late introduction of the C20 alcohol that mirrors the biosynthesis of this compound. The key steps involved a high yielding cross metathesis reaction between enone 6 and alkene 7 to give E-enone 4 and a Mn-catalyzed conjugate reduction α-oxidation reaction to introduce the C20 hydroxyl group. Acid treatment of the α-hydroxyketone 4 gave spiroketal 19 which was converted into known spirangien A (1) advanced intermediate spiroketal 3.
authors: School of Chemistry, The Bio21 Institute, The University of Melbourne, Victoria 3010, Australia.
authors: Claire
authors: C
authors: Gregg
authors: Christian
authors: C
authors: Gunawan
authors: Audrey Wai Yi
authors: AW
authors: Ng
authors: Samantha
authors: S
authors: Wimala
authors: Sonali
authors: S
authors: Wickremasinghe
authors: Mark A
authors: MA
authors: Rizzacasa
mesh_terms: D000080:Acetals / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009231:Myxococcales / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000080:Acetals; D005231:Fatty Acids, Unsaturated; D005663:Furans; D013141:Spiro Compounds; C523683:spirangien A; C520774:spiroketal