Beta-hydroxy-gamma-lactones as chiral building blocks for the enantioselective synthesis of marine natural products.
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.
García
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Instituto Universitario de Bio-Orgánica Antonio González, Universidad de La Laguna, C/Astrofísico Francisco Sánchez, 2, 38206 La Laguna, Tenerife, Spain.
Martín
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T
Martín
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VS
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D008386:Marine Biology; D000459:Phaeophyceae / Q000737:chemistry*; D013057:Spectrum Analysis; D013237:Stereoisomerism
D001688:Biological Products; D007783:Lactones