Modeling the Effect of Substitution on the Pb(OAc)4 Mediated Oxidative Cleavage of Steroidal 1,2-Diols

• Published in: Journal of organic chemistry Vol. 70; no. 18; pp. 7080 - 7086
• Main Authors: Öztürk, C, Topal, K, Aviyente, V, Tüzün, Nurcan Ş, Sánchez Fernández, E, Arseniyadis, S
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 02.09.2005; Amer Chemical Soc
• Subjects: Alicyclic compounds, terpenoids, prostaglandins, steroids; Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Steroids; ELEMENTS; MOLECULAR CALCULATIONS; PATTERN; EFFECTIVE CORE POTENTIALS; HETERO-DOMINO TRANSFORMATIONS; DERIVATIVES; SOLVENT; Substituent effect; Steroid; Diol; Electrophilic addition; Lead Acetate; Oxygen heterocycle; Modeling; Density functional method; Cleavage; Oxidation; Ethylenic compound; Lead complex; Successive reaction

We comment on the effects of angular substitution on the outcome of a Pb(OAc)4 (LTA) mediated heterodomino reaction, with selected bicyclic unsaturated 1,2-diols, which is considered to proceed through a series of transformations in a single vessel. The first two, oxidative and pericyclic, are follo...