ChemInform Abstract: Synthesis of (22R,23R,24S) -24-Methyl-5α-cholestane-3β,6α,22,23-tetraol, a Biosynthetic Precursor of Brassinolide

Autor:	Vladimir N. Zhabinskii, N. D. Pavlovskii, Vladimir A. Khripach
Rok vydání:	2010
Předmět:	Chemistry Stereochemistry medicine.medical_treatment General Medicine Ring (chemistry) Cyclopropane Steroid chemistry.chemical_compound Hydroboration Side chain medicine Cholestane Enone Brassinolide
Zdroj:	ChemInform. 33
ISSN:	1522-2667 0931-7597
Popis:	A biosynthetic precursor of brassinolide, (22R,23R,24S)-24-methyl-3α-cholestane-3β,6α,22,23-tetraol was synthesized from Δ23-22-keto steroid which was obtained from the corresponding 20-carbonitrile oxide. The side chain was built up by a series of successive transformations: hydride reduction of the initial enone, epoxidation of the allyl-like alcohol, and copper(I) cyanide-catalyzed opening of the 23,24-epoxy ring. The cyclic fragment was completed by opening of the cyclopropane ring with subsequent hydroboration and oxidation of the Δ5-bond.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::2bde12cfdd318b4d97ee636343d3d003 https://doi.org/10.1002/chin.200227218 Zobrazit plný text záznamu Plný text