60078-92-4Relevant articles and documents
Lipase-mediated resolution of the hydroxy-cyclogeraniol isomers: application to the synthesis of the enantiomers of karahana lactone, karahana ether, crocusatin C and γ-cyclogeraniol
Serra, Stefano,Gatti, Francesco G.,Fuganti, Claudio
experimental part, p. 1319 - 1329 (2009/12/01)
A comprehensive study on the lipase PS-mediated resolution of different hydroxy-geraniol isomers is reported. A number of α-, β- and γ-isomers bearing a 2-, 3- or 4-hydroxy functional group were synthesised regioselectively and then submitted to the lipase-mediated kinetic acetylation. The latter experiments showed that the 2-hydroxy isomers 4, 5 and 14 (α, γ and β, respectively) as well as cis-3-hydroxy α-cyclogeraniol 7 and cis-4-hydroxy γ-cyclogeraniol 10 could be easily resolved by this procedure. The enantiomeric purity of the main part of these compounds was increased by recrystallisation and the enantiopure diols obtained were used as building blocks for the synthesis of the natural terpenoids karahana lactone, karahana ether and crocusatin C and for the preparation of the synthetic intermediate γ-cyclogeraniol. The absolute configurations of the enantiomers of the diols 7, 10, 14 and 19 were determined by chemical correlation with the known compounds 40, 41, 39 and 41, respectively.
Enantioselective synthesis of 1(R)-hydroxypolygodial
Della Monica, Carmela,Della Sala, Giorgio,D'Urso, Deborah,Izzo, Irene,Spinella, Aldo
, p. 4061 - 4063 (2007/10/03)
Enantioselective preparation of 1(R)-hydroxypolygodial (5) has been achieved starting from α-ionone through a synthetic strategy involving a Corey-Bakshi-Shibata oxazaborolidine-mediated reduction and a stereoselective Diels-Alder reaction as key steps.
Synthetic scheme for the preparation of 13C-labeled 3,4-didehydro-retinal, 3-hydroxyretinal, and 4-hydroxyretinal up to uniform 13C-enrichment
Van Wijk, Arjan A. C.,Van de Weerd, Michiel B.,Lugtenburg, Johan
, p. 863 - 868 (2007/10/03)
A modular synthetic scheme has been developed for the synthesis of 13C-labeled naturally occurring visual pigment chromophores; 3,4-didehydroretinal, 3-hydroxyretinal, and 4-hydroxyretinal. These compounds can now be made with > 99% 13C enrichment at any position or combination of positions. We used the common C10+C5+C5 scheme for the synthesis of retinals, and by making variations in the C10 part we can now prepare the desired retinal derivatives with selective or uniform 13C enrichment. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
γ-Pyronene, a synthon derived from saffron and intermediary precursor of synthesis of forskolin and strigol
Boulin,Arreguy-San Miguel,Delmond
, p. 2753 - 2762 (2007/10/03)
γ-Pyronene, a terpenic synthon available from myrcene, is an excellent raw material for the preparation of numerous intermediates used in the synthesis of perfumes, retinoids and biological derivatives such as forskolin or strigol.
A synthetic approach to (+/-)-forskolin. Part I. Preparation of key hydrobenzofuran intermediates
Anies, Claude,Pancrazi, Ange,Lallemand, Jean-Yves
, p. 183 - 202 (2007/10/03)
In a synthetic approach to (+/-)-forskolin 1, a stereoselective preparation of the unsaturated lactone 2 was envisaged.Propargylic derivatives 18a-c were prepared from available α-ionone 5 and treated with Bu3SnH/AIBN to give the bicyclic vinylstannanes 19a-c in high yield.From these compounds we then performed transmetallation reactions to obtain the 21a-c and 22b homologous derivatives.The two enyne compounds 29 and 30 were then prepared by our previous approach to lactone 2 involving a radical C7-C8 bond formation.In a second radical approach promoted by SmI2, the diol 10, was used to synthesize a potential precursor of the dialdehyde 9. - Keywords: forskolin; tributylstannane; radical cyclization; transmetallation; vinylstannane; vinyl iodide; Pd(0) coupling reaction
Microbial synthesis of optically pure (R)-2,4,4-trimethyl-3-(2'-hydroxyethyl)-cyclohex-2-en-1-ol, a new and versatile chiral building block for terpene synthesis
Aranda,Bertranne,Azerad,Maurs
, p. 675 - 678 (2007/10/02)
The hydroxylation of 2,4,4-trimethyl-3-(2'-hydroxyethyl)-2-cyclohexene by Mucor plumbeus, after usual work up and a subsequent single crystallization, gave the corresponding optically pure (1R)-hydroxy synthon.
Synthesis and biological evaluation of A-ring analogs of the natural germination stimulant strigol
Mangnus, E. M.,Zwanenburg, B.
, p. 155 - 159 (2007/10/02)
An A-ring-derived analog of the natural germination stimulant, Strigol (1), has been prepared from citral in an unambiguous manner.This analog, 2, a γ-hydroxy aldehyde for which a high stimulant activity was claimed in the literature, has been re-evaluate
An Intramolecular Diels-Alder Strategy to Forskolin
Nicolaou, K. C.,Li, Wen Sen
, p. 421 (2007/10/02)
A strategy for the construction of the AB ring system of forskolin based on a novel intramolecular Diels-Alder reaction is reported.
