کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1350774 | 980467 | 2006 | 4 صفحه PDF | دانلود رایگان |

An enantiospecific synthesis of (−)-2-hydroxy-exo-brevicomin was achieved from l-(+)-tartaric acid in high yield. The key step involves a very highly diastereoselective reduction of a keto Weinreb amide.
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(+)-(4R,5R)-5-(Pent-4-enoyl)-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamideC13H21NO5[α]D = +4.4 (c 3.6, CHCl3)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (4R,5R)
(−)-(4R,5R)-5-((R)-1-tert-Butyldimethylsilyloxypent-4-enyl)-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamideC19H37NO5Si[α]D = −9.5 (c 2.1, CHCl3)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (4R,5R)
(+)-(4R,5R)-5-((R)-1-tert-Butyldimethylsilyloxypent-4-enyl)-4-acetyl-2,2-dimethyl-1,3-dioxolaneC18H34NO4Si[α]D = +12.7 (c 1.1, CHCl3)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (4R,5R)
(−)-2-Hydroxy-exo-brevicominC17H30O4[α]D = −32 (c 0.5, CHCl3)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (1S,2R,5R,7S)
Journal: Tetrahedron: Asymmetry - Volume 17, Issue 5, 6 March 2006, Pages 850–853