- Concise syntheses of the natural products (+)-sylvaticin and (+)-cis-sylvaticin
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Two concise syntheses of the natural products cis-sylvaticin and sylvaticin are reported, using oxidative cyclization methodology as the key step. A sequential solvolysis/hydride shift/intramolecular reduction cascade was used to establish the trans stereochemistry of one of the THF rings of sylvaticin.
- Donohoe, Timothy J.,Harris, Robert M.,Williams, Oliver,Hargaden, Grainne C.,Burrows, Jeremy,Parker, Jeremy
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scheme or table
p. 12854 - 12861
(2010/01/29)
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- Asymmetric dihydroxylation affords enantiomerically pure c12 building blocks from trans,trans,cis-1,5,9-cyclododecatriene
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Through sequential catalytic asymmetric dihydroxylation (AD), t,t,c-1,5,9-cyclododecatriene is transformed into functionalized cyclic cis-olefins with high enantio- and diastereocontrol. To demonstrate their synthetic utility as sources for open chain C12 building blocks, one such intermediate is converted into an α,ω-diester in which the chain ends are differentiated.
- Hugger, Uwe
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p. 6603 - 6606
(2007/10/02)
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- Selective Asymmetric Dihyroxylation of Polyenes
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The asymmetric dihydroxylation procedure (AD) is applied to a variety of polyenes.In many cases excellent regioselectivities are obtained.The observed selectivities are rationalized in terms of electronic and/or steric inherent to the substrate, superimposed on the substrate's favorable or unfavorable interactions with the binding pocket of the AD ligand.Surprisingly, for medium and large ring olefins with trans-double bonds outstanding enantioselectivities are realized using the pyrimidine ligands.A hexaol of D3 symmetry is prepared from all trans cyclodecatriene.
- Becker, Heinrich,Soler, Marcos A.,Sharpless, K. Barry
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p. 1345 - 1376
(2007/10/02)
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- SYNTHESIS OF 1,2-CYCLOALKANEDIOLS BY INTRAMOLECULAR TITANIUM-INDUCED PINACOL COUPLING
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Seven representative 1,2-cycloalkanediols of ring size 6-14 were prepared in high yield by titanium-induced pinacol coupling of dialdehydes.Cis stereochemistry predominated in six- and eight-membered rings, but trans products were formed in ring sizes ten and above.
- McMurry, John E.,Rico, Joseph G.
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p. 1169 - 1172
(2007/10/02)
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