Synthesis and Chemistry of 2,3-Dioxabicyclo[2.2.2]octane-5,6-diols

Abstract

iiiDeclaration v Acknowledgments vi

Stereocontrolled Synthesis of the cis‐Hydroxydecalin System: Towards Biologically Active 19‐nor‐Clerodanes

“…Installation of the C-5-hydroxy moiety was executed through a hetero [4+2]-cycloaddition of diene 14 with singlet oxygen promoted by Rose Bengal bis(triethylammonium) salt photosensitization. [14] As predicted, the addition occurred exclusively from the less hindered β-face to afford 13 in 69 % yield, as confirmed by X-ray crystal structure analysis (Scheme 4). Scheme 4.…”

Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products

“…The double bond in the 1,2-dioxene ring of 321 was subjected to dihydroxylation with osmium tetroxide (Scheme 92) [354,365]. The reaction was performed in aqueous tert -butanol, acetone, or acetonitrile at room temperature.…”

“…For example, the commercially available AD-mix, a mixture consisting of K 2 OsO 2 (OH) 4 (catalytic amounts, a source of OsO 4 ) and K 3 Fe(CN) 6 (oxidizer), was employed for this purpose. In this reaction, K 2 OsO 4 (0.5 mol %) combined with oxidizers (K 3 Fe(CN) 6 , N -methylmorpholine N -oxide, citric acid, or KClO 3 ) was also used [354,365]. …”

2-C-Phenylerythrono-1,4-lactone

“…For background on the leaf-closing substance of the tropical legume Leucaena leucocephalam, see: Ueda et al (2001); Gogoi & Argade (2004); Koumbis et al (2006). For the synthesis of polyhydroxyated compounds from 1,2-dioxines, see: Robinson et al (2006Robinson et al ( , 2009; Valente et al (2009); Pedersen et al (2009).…”