title: How a diversity-oriented approach has inspired a new hypothesis for the gabosine biosynthetic pathway. A new synthesis of (+)-gabosine C.
abstract: A new synthesis of (+)-gabosine C has been accomplished as part of a general diversity-oriented approach that also delivered the previously unknown (-)-4-epi-gabosine C. The identification of the unexpected intermediate (+)-8, together with the isolation of ketones 9 and 10 in previous investigations, prompted us to formulate a new hypothesis for the biosynthesis of gabosines, based on a keto-enol equilibrium cascade pathway starting from 2-epi-5-epi-valiolone, along which the necessary precursors for all the different types of gabosines are generated.
authors: Universitat Autònoma de Barcelona, Departament de Química, 08193 Bellaterra, Spain. pau.bayon@uab.es marta.figueredo@uab.es.
authors: Miguel Ángel
authors: MÁ
authors: Fresneda
authors: Ramon
authors: R
authors: Alibés
authors: Josep
authors: J
authors: Font
authors: Pau
authors: P
authors: Bayón
authors: Marta
authors: M
authors: Figueredo
mesh_terms: D003511:Cyclohexanols / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D003511:Cyclohexanols; D003512:Cyclohexanones; D007659:Ketones; C006021:KD 16U1