An improved synthesis of azedarachol

• Published in: Steroids Vol. 186; pp. 109072 - 109076
• Main Authors: Ran, Gao, Weisheng, Tian
• Format: Journal Article
• Language: English
• 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

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...