Synthesis of Rationally Designed Mechanism-Based Inactivators of the (S)-Adenosyl-L-methionine: Δ²⁴(25)₋ Sterol Methyl Transferase

Abstract

A series of 26,27-cyclopropylidine side chain modified sterols were prepared for the first time from the known aldehydes by Wittig olefination with the ylide from cyclopropyltriphenylphosphonium bromide in butyllithium. Two novel by-products were detected; sterols with nine carbon side chains which lack the terminal isopropyl group and with double bonds in positions 23,24 or 24,25. The structures of the compounds were confirmed by a combination of chromatographic (GLC and HPLC) and spectral (IR, ¹H, ¹³C-NMR) methods.

^#Visiting Professor from the Department of Pharmacognosy, Beijing Medical University, Beijing 100083, China

Notes

^#Visiting Professor from the Department of Pharmacognosy, Beijing Medical University, Beijing 100083, China