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Preparation of desmosterol from fucosterol

, : Preparation of desmosterol from fucosterol. Chemical and Pharmaceutical Bulletin (Tokyo) 24(8): 1928-1931

Desmosteryl acetate, a useful key intermediate for synthesis of metabolites of vitamin D3, was synthesized from fucosterol by 2 routes: 24, 28-epoxyfucosteryl acetate was treated with solid acids such as zeolite, silica-alumina and alumina-boria to give desmosteryl acetate in a yield of 16%-40%; dehydration of 24-hydroxycholesteryl acetate, which was obtained by ozonolysis of fucosteryl acetate followed by reduction with sodium borohydride with P2O5 in benzene afforded desmosteryl acetate in a yield of 85%.

Accession: 006173031

DOI: 10.1248/cpb.24.1928

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Related references

Chen, S.; Nakanishi, K.A.ata, N.M.risaki, M.I.ekawa, N.S.imizu, Y., 1975: Stereospecificity in the conversion of fucosterol 24,28-epoxide to desmosterol in the silkworm, Bombyx mori. Journal 97 (18) 5297-5299

Fujimoto, Y.; Morisaki, M.; Ikekawa, N., 1975: Studies on steroids. Part XXIX. Synthesis of allenic analogues fucosterol and desmosterol. Journal of the Chemical Society. Perkin Transactions 1: 2303-2307

Fujimoto Y.; Ikuina Y.; Kakinuma K., 1989: Mechanism of the conversion of fucosterol epoxide into desmosterol in insects stereochemical fate of the diastereotopic c 26 and c 27 methyl groups of the epoxide. Journal of the Chemical Society Chemical Communications (8): 464-466

Nicotra F.; Pizzi P.; Ronchetti F.; Russo G.; Toma L., 1981: Substrate stereospecificity in the metabolism of fucosterol and iso fucosterol 24 28 epoxides in tenebrio molitor. The insect T. molitor is able to convert the (24R,28S)-isofucosterol epoxide into cholesterol much better than the (24S,28R)-isomer; the (24R,28R)- and the (24S,28S)-fucosterol epoxides are transformed into cholesterol at about the same extent.

Allais, J.; Barbier, M., 1977: Fucosterol 24,28 epoxide, an intermediary in the oxidative biodegradation of fucosterol in cholesterol by the locust Locusta migratoria (R. and F.)

Allais, J.P.; Barbier, M., 1977: Fucosterol-24,28-epoxide, an intermediate in the oxidative biodegredation of fucosterol to cholesterol by the cricket (Locusta migratoria (R. and F.). beta-Sitosterol 1 is metabolised to cholesterol 5 by phytophagous insects. It has been previously shown that fucosterol-24,28 epoxide 3 is transformed into 5 in Locusta migratoria, desmosterol 4 being an intermediate. It is now established that lo...

Allais J P.; Barbier M., 1977: Fucosterol 24 28 epoxide an intermediate compound in the oxidative bio degradation of fucosterol in cholesterol by the locust locusta migratoria. Febs Letters 82(2): 333-336

Shimadate, T.; Rosenstein, F.U.; Kircher, H.W., 1977: Preparation of fucosterol from giant kelp. Commercial extraction of alginic acid from Macrocystis pyrifera leaves a residue that is a good source of fucosterol, 5,24(28)E-stigmastadien-3.beta.-ol. The isolation and purification of this sterol is described.

Dasgupta, S.K.; Crump, D.R.; Gut, M., 1974: New preparation of desmosterol. Journal of Organic Chemistry 39(12): 1658-1662

Ikuina Y.; Kanzawa Y.; Fujimoto Y.; Kakinuma K., 1989: Preparation of 26 carbon 13 desmosterol. (26-13C)Desmosterol (1) and its 3-benzoate (8) and 3-tert-butyldimethylsilyl ether (9) were synthesized starting with (1-13C)propionic acid and a steroidal C-24 aldehyde (2).