An improved synthesis of azedarachol

An improved synthesis of azedarachol is reported in 10 steps with an overall yield of 12% from pregnanetriol. A proper use of p-anisaldehyde dimethyl acetal provided a chance of regioselective reduction of 2-enepregnane-16R,20R-p-anisaldehyde acetal(6) and in turn allowed a selective protection at C...

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Bibliographic Details
Published inSteroids Vol. 186; pp. 109072 - 109076
Main Authors Ran, Gao, Weisheng, Tian
Format Journal Article
LanguageEnglish
Published NEW YORK Elsevier 01.10.2022
Subjects
Biochemistry & Molecular Biology
Endocrinology & Metabolism
Life Sciences & Biomedicine
Science & Technology
PROTECTING-GROUP
Synthesis
Azedarachol
STEREOSELECTIVE-SYNTHESIS
Stereoselective reduction
Pregnanetriol
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Summary:An improved synthesis of azedarachol is reported in 10 steps with an overall yield of 12% from pregnanetriol. A proper use of p-anisaldehyde dimethyl acetal provided a chance of regioselective reduction of 2-enepregnane-16R,20R-p-anisaldehyde acetal(6) and in turn allowed a selective protection at C16-hydroxy and enabled a stereoselective reduction of C20-ketone to establish the configuration at C20.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0039-128X
1878-5867
1878-5867
DOI:10.1016/j.steroids.2022.109072