An improved synthesis of azedarachol

Gao Ran; Tian Weisheng

doi:10.1016/j.steroids.2022.109072

An improved synthesis of azedarachol

Steroids. 2022 Oct:186:109072. doi: 10.1016/j.steroids.2022.109072. Epub 2022 Jun 20.

Authors

Gao Ran¹, Tian Weisheng²

Affiliations

¹ School of Chemistry and Materials Science, Huaibei Normal University, Huaibei 235000, China. Electronic address: xizhugaoran@163.com.
² CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.

PMID: 35738310
DOI: 10.1016/j.steroids.2022.109072

Abstract

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.

Keywords: Azedarachol; Pregnanetriol; Stereoselective reduction; Synthesis.

MeSH terms

Ketones*
Stereoisomerism

Substances

Ketones