- A convergent stereocontrolled synthesis of [3-14C]solanesol
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In this communication, we report the synthesis of 5 mCi of [3- 14C]solanesol (1) prepared from ethyl [3-14C]acetoacetate and (all-E)-octaprenyl bromide (2) in four steps, with a specific radioactivity of 19.83 mCi/mmol and with a chemical/ stereochemical and radiochemical purity of ≥ 95%. (Figure 1). Position 3 of the chain was selected for 14C labelling because of the metabolic stability of this position. Unlabelled (all-E)-octaprenyl (18) (Scheme 4) necessary for this work was prepared via a convergent iterative 'allyl-allyl' coupling approach of precursors easily derived from readily available inexpensive starting materials. Copyright
- Roe, Stephen J.,Oldfield, Mark F.,Geach, Neil,Baxter, Andrew
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p. 485 - 491
(2014/03/21)
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- Novel regio- and stereoselective cascade 6-endo-trig cyclisations from polyene acyl radical intermediates leading to steroid-like pentacycles and heptacycles
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In a quite remarkable regio- and stereoselective manner, each of the (all-E)-polyene selenoates 5a-c is shown to undergo cascade radical-mediated polycyclisations via consecutive 6-endo-trig reactions, leading to the corresponding all-trans, anti, tri-, penta- and heptacycles, i.e., 20, 23, and 25, in good yields. The configurations of these 'steroid-like' polycycles followed from detailed examination and correlation of chemical shift data in their 13C-NMR spectra.
- Handa, Sandeep,Nair, Prathap S.,Pattenden, Gerald
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p. 2629 - 2643
(2007/10/03)
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- Novel cascade of seven radical-mediated 6-endo-trig cyclisations leading to a unique all-trans, anti heptacycle
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A cascade of seven radical-mediated 6-endo-trig cyclisations from the all-E-heptaene selenoate ester 1 results in the production of the all-trans, anti heptacycle 2 together with the isolation of the all-trans, anti tetracycle 15.
- Handa, Sandeep,Pattenden, Gerald
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p. 843 - 845
(2007/10/03)
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- STEREOSPECIFIC SYNTHESIS OF OCTAPRENOLS WT3C4OH AND WT3C3TOH
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A total synthesis of the above prenols has been carried out.
- Grigor'eva, N. Ya.,Pinsker, O. A.,Moiseenkov, A. M.
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p. 2045 - 2050
(2007/10/02)
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- β,γ-dihydropolyprenyl alcohol derivatives and pharmaceutical composition containing a polyprenyl compound
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A β,γ-dihydropolyprenyl alcohol derivative having the formula: STR1 wherein n is an integer of 5 to 7 and R is hydrogen, a lower alkyl group or an aliphatic or aromatic acyl group, is new and useful as a phylactic agent against human and animal infectious diseases. Other disclosed polyprenyl compounds are also useful as such agents.
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- Stereoselective Synthesis of Solanesol and all-trans-Decaprenol
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Allylic p-tolyl sulphonates (5), (14), and (16) couple with allylic bromide (7) and geranyl bromide to produce regio- and stereo-chemically pure 1,5-diene systems.The coupling of all-trans-ω-bromogeranyl acetate (7) with geranyl p-tolyl sulphone (5) and higher isoprenologues (21), (24), and (27), followed by reductive elimination of p-tolylsulphonyl group, furnishes a stereoselective synthesis of all-trans-polyprenols (3), (23), (26), and decaprenol (1b).Solanesol (1a) was synthesised using trans-4-chloroprenyl acetate (29) instead of (7).
- Sato, Kikumasa,Inoue, Seiichi,Onishi, Akira,Uchida, Nobuhiko,Minowa, Nobuto
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p. 761 - 769
(2007/10/02)
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- Hypertension treating agent containing polyprenyl alcohol
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This invention relates to a hypertension treating agent comprising a polyprenyl alcohol or an ester thereof of the general formula: STR1 wherein n represents an integer of 7-10 and A represents a group of the general formula: STR2 in which a and b each represent hydrogen or they may form a bond, or STR3 in which R represents hydrogen or --COR', R' being a saturated or unsaturated aliphatic hydrocarbon group of 1-17 carbon atoms; cyclohexyl group; unsubstituted phenyl group or phenyl group substituted with a halogen atom or a lower alkoxy group; (halogen atom-substituted phenoxy)-lower alkyl group; or pyridyl group.
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