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Synlett 2011(8): 1149-1150
DOI: 10.1055/s-0030-1259943
DOI: 10.1055/s-0030-1259943
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Biomimetic Synthesis of (+)-Neroplofurol
Further Information
Publication History
Received
31 December 2010
Publication Date:
07 April 2011 (online)
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.
Key words
Sharpless dihydroxylation - Shi epoxidation - cascade reaction - atom economic - biomimetic synthesis
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- Supporting Information