Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2009, Issue 29, Pages 5038-5046Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200900772
Keywords
Amino acids; Asymmetric synthesis; Epoxides; Natural products; Quaternary stereocenters
Categories
Funding
- National Natural Science Foundation of China [20832005, 20602008]
- Fudan University [EYH1615003, EYH1615004]
Ask authors/readers for more resources
A flexible common approach for the asymmetric syntheses of sphingofungins E and F is reported, with efficient use of both diastereomers of the Baylis-Hillman adduct in a stereoconvergent manner. Pronounced steric effects of the 2-substituents in diastereoselective dihydroxylations of (E)-2-hydroxymethyl-2,3-alkenoates were observed. This strategy also allowed full control over the absolute configurations of the quaternary stereocenters in alpha-substituted amino acids through tunable site-specific adjustment of oxidation states. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available
Share Paper
