García C, Martín T, Martín V S
Instituto Universitario de Bio-Orgánica Antonio González, Universidad de La Laguna, C/Astrofísico Francisco Sánchez, 2, 38206 La Laguna, Tenerife, Spain.
J Org Chem. 2001 Feb 23;66(4):1420-8. doi: 10.1021/jo0057194.
The enantioselective synthesis of trans-(+)-laurediol, (2S,3S,5R)-5-[(1R)-1-hydroxy-9-decenyl]-2-pentyltetrahydro-3-furanol, and (2S,3S,5S)-5-[(1S)-1-hydroxy-9-decenyl]-2-pentyltetrahydro-3-furanol are described. In addition, a formal synthesis of trans-(-)-kumausyne is also developed. All the synthetic procedures have in common the use of enantiomerically enriched beta-hydroxy-gamma-lactones, easily available by Sharpless asymmetric dihydroxylation (AD) from the suitable beta,gamma-unsaturated ester. The use of Katsuki-Sharpless asymmetric epoxidation (AE) as an additional enantioselective reaction provides cyclic compounds of high enantiomeric purity.
描述了反式-(+)-月桂二醇、(2S,3S,5R)-5-[(1R)-1-羟基-9-癸烯基]-2-戊基四氢-3-呋喃醇和(2S,3S,5S)-5-[(1S)-1-羟基-9-癸烯基]-2-戊基四氢-3-呋喃醇的对映选择性合成。此外，还开发了反式-(-)-久马素的形式合成。所有合成方法的共同之处在于使用对映体富集的β-羟基-γ-内酯，可通过夏普莱斯不对称双羟基化（AD）从合适的β,γ-不饱和酯轻松获得。使用胜木-夏普莱斯不对称环氧化（AE）作为额外的对映选择性反应可提供高对映体纯度的环状化合物。
