Synlett 2011(8): 1149-1150  
DOI: 10.1055/s-0030-1259943
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Biomimetic Synthesis of (+)-Neroplofurol

Xing Huo*a, Xinfu Pana, Guosheng Huanga, Xuegong Shea
Department of Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
Fax: +86(931)8912582; e-Mail: huox@lzu.edu.cn;
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Publication History

Received 31 December 2010
Publication Date:
07 April 2011 (online)

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Abstract

(+)-Neroplofurol was biomimetically synthesized in only two steps from natural (+)-nerolidol via Sharpless dihydroxylation and a cascade Shi epoxidation/epoxide ring-opening reaction. All carbons are derived from natural (+)-nerolidol and no protecting groups were utilized, making the synthesis atom-economical and highly efficient. The synthetic neroplofurol was proved to be the enantiomer of the natural one, according to ¹H NMR, ¹³C NMR spectra and optical rotation value. The absolute configuration of natural neroplofurol was also deduced to be 3R,6S,7R,10S.

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