A concise synthesis of beta-sitosterol and other phytosterols.
A convenient synthesis of sidechain-modified phytosterols is achieved via a temporary masking of the stigmasterol 5,6-alkene as an epoxide. Following performance of the desired modification, the alkene is regenerated through a mild deoxygenation. The approach is applied to the syntheses of beta-sitosterol and campesterol acetate, and suggests a facile route to the (Z)-isomers of Delta(22-23) phytosterols.
Hang
Jiliang
J
Department of Chemistry, University of Nebraska-Lincoln, 809 Hamilton Hall, Lincoln, NE 68588-0304, USA.
Dussault
Patrick
P
D000475:Alkenes / Q000737:chemistry; D002784:Cholesterol / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D010840:Phytosterols / Q000138:chemical synthesis / Q000737:chemistry; D012855:Sitosterols / Q000138:chemical synthesis* / Q000737:chemistry*
D000475:Alkenes; D004852:Epoxy Compounds; D010840:Phytosterols; D012855:Sitosterols; C021273:campesterol; C025473:gamma-sitosterol; D002784:Cholesterol