Ring-Closing Metathesis-Based Synthesis of (3R,4R,5S)-4-Acetylamino-5-amino-3-hydroxy- cyclohex-1-ene-carboxylic Acid Ethyl Ester: A Functionalized Cycloalkene Skeleton of GS4104
- 6 June 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 71 (14), 5365-5368
- https://doi.org/10.1021/jo060633h
Abstract
(3R,4R,5S)-4-Acetylamino-5-amino-3-hydroxy-cyclohex-1-ene-carboxylic acid ethyl ester, a functionalized cyclohexene skeleton of GS4104, was diastereoselectively synthesized. A major advantage of this synthesis is the use of readily available l-serine to replace frequently used (−)-shikimic acid or (−)-quinic acid as the starting material. Ring-closing metathesis and diastereoselective Grignard reactions successfully served as the key steps. Absolute configurations of the key intermediates were confirmed by corresponding two-dimensional NMR studies.Keywords
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