Polyhydroxylated pyrrolizidines. Part 3: A new and short enantiospecific synthesis of (+)-hyacinthacine A2 |
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Authors: | Isidoro Izquierdo María T Plaza Francisco Franco |
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Institution: | Department of Medicinal and Organic Chemistry. Faculty of Pharmacy. University of Granada, Granada 18071, Spain |
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Abstract: | (1R,2R,3R,7aR)-1,2-Dihydroxy-3-hydroxymethylpyrrolizidine (+)-Hyacinthacine A2 1 has been synthesized by Wittig's methodology using (2′S,3′R,4′R,5′R)-3′,4′-dibenzyloxy-N-tert-butyloxycarbonyl-5′-tert-butyldiphenylsilyloxymethylpyrrolidin-2′-yl]carbaldehyde 3, prepared from a partially protected DMDP 2, and the appropriated ylide, followed by cyclization by an internal reductive amination process of the resulting unsaturated aldehyde 4 and total deprotection. |
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