Total synthesis of (±)-specionin

Leonard, John; Hussain, Nigel

doi:10.1039/p19940000061

Cited by 11 publications

(8 citation statements)

References 12 publications

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“…13b In the second example (ii), cis -bicyclo[3.3.0]octenone 11 was dihydroxylated also preferentially from the concave face to give diol 12 with relatively low 4:1 selectivity. 14 It was hypothesized in this report that the selectivity may be due to a directing effect of the carbonyl group, as conversion of the ketone into a protected β-alcohol inverts the facial selectivity.…”

Section: Resultsmentioning

confidence: 94%

Origins of Stereoselectivities of Dihydroxylations of cis-Bicyclo[3.3.0]octenes

et al. 2012

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Stereoselectivities of the dihydroxylations of cis-bicyclo[3.3.0]octene intermediates for a projected total synthesis of chromodorolide A have been explored experimentally. The reaction occurs unexpectedly on the apparently more hindered (concave) face; this result has been explained through computational studies using B3LYP and B3LYP-D3 methods. Torsional effects are largely responsible for the stereoselectivity encountered in the chromodorolide A synthesis. Many literature examples have been reported on related cases. QM calculations show that the stereoselectivities of dihydroxylations of fused cyclopentenes are influenced by the conformational rigidity or flexibility of the substrate. Torsional, electrostatic, and steric effects can all influence stereoselectivity, and the rigidity or flexibility of conformations of reactants provides a predictive guide to stereoselectivity.

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Section: Resultsmentioning

confidence: 94%

Origins of Stereoselectivities of Dihydroxylations of cis-Bicyclo[3.3.0]octenes

et al. 2012

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“…Heterogenization of these homogeneous catalysts stabilizes the metalloporphyrin or enhances the catalytic performance by preventing the formation of inactive dimers. On the other hand, such immobilization can influence the chemoselectivity, regioselectivity and stereoselectivity of the catalyzed reaction [12][13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Oxidation of alcohols with sodium periodate catalyzed by supported Mn(III) porphyrins

Tangestaninejad

Mirkhani

Karami

et al. 2006

JICS

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The mild and efficient oxidation of alcohols with sodium periodate catalyzed by manganese(III) tetrakis(p-sulfonatophenylporphyrinato) acetate, [Mn(TPPS)], supported on polyvinylpyridine, [Mn(TPPS)-PVP], and Amberlite IRA-400, [Mn (TPPS)-Ad IRA-400], at room temperature is reported. The catalysts used in this study showed high activity not only in the oxidation of benzylic and linear alcohols but also in the oxidation of secondary alcohols at room temperature. These catalysts can be reused several times without significant loss of their activity.

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“…Such immobilization makes the catalysts separable from reaction mixtures and reusable, enhance the catalyst stability towards oxidation and allow preparation of environmentally friendly catalysts. Many heterogenized metalloporphyrin catalysts have been reported for alkene epoxidation and alkane hydroxylation [ 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 ].…”

Section: Introductionmentioning

confidence: 99%