- 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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- 2α,4-Dihydroxy-1,8-cineole. A New Possum Urinary Metabolite
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2α,4-Dihydroxy-1,8-cineole (2a) is present in the urine of brushtail possums fed a diet enhanced with 1,8-cineole (1).Chemical syntheses of this novel metabolite (2a) and its 2β-epimer (19a) are described.The n.m.r. spectra of various 1,8- and 1,4-cineoles are reported, and literature assignments for C1 and C4 in the 1,4-cineole series are corrected.
- Carman, Raymond M.,Rayner, Anthony C.
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p. 2087 - 2098
(2007/10/02)
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- 1-Acetyl-4-methyl-3-cyclohexen-1-ol, a useful precursor in the synthesis of cyclic monoterpenes
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A synthesis of monocyclic monoterpenes: p-mentha-1,8-dien-4-ol (1), terpinolene (4) and p,α-dimethylstyrene (5) from the titled compound 7, as a common precursor, is reported.
- Andrade,Munoz,Tamariz
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p. 1603 - 1609
(2007/10/02)
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- Preparation of 2-exo-Hydroxy-7-oxabicyclo[2.2.1]heptanes
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2-exo-Hydroxy-7-oxabicyclo[2.2.1]heptanes are prepared by treating the corresponding cis-epoxycyclohexanol with acid in an inert solvent or by treating a 3-cyclohexen-1-ol which will produce the corresponding cis-epoxy alcohol successively or concurrently with an oxidizing agent and an acid in an inert solvent.
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- LEWIS ACID CATALYSED PINACOL REARRANGEMENT - A SHORT SYNTHESIS OF KARAHANAENONE
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The pinacolic coupling reaction has been effectively used to prepare the unsymmetrical pinacol 2 and this key intermediate underwent a smooth ring enlargement to the monoterpene karahanaenone 3, an odoriferous constituent of Japanese hop and Cypress oil.
- Bhushan, Vidya,Chandrasekaran, Srinivasan
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p. 1537 - 1538
(2007/10/02)
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