Synthesis of rationally designed mechanism-bsed inactivators of the (S)-adenosyl-L-methionine: Δ(24(25))-sterol methyl transferase

Zhonghua Jia, Wen Zhou, Dean Guo, W. David Nes

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

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.

Original languageEnglish
Pages (from-to)3841-3848
Number of pages8
JournalSynthetic Communications
Volume26
Issue number20
DOIs
StatePublished - 1996

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