β-Hydroxy-γ-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 β-hydroxy-γ-lactones, easily available by Sharpless asymmetric dihydroxylation (AD) from the suitable β,γ-unsaturated ester. The use of Katsuki−Sharpless asymmetric epoxidation (AE) as an additional enantioselective reaction provides cyclic compounds of high enantiomeric purity.
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| Main Authors: | , , |
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| Other Authors: | |
| Format: | artículo biblioteca |
| Language: | English |
| Published: |
American Chemical Society
2001-01-17
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| Subjects: | Ethers, Tetrahydrofurans, Alcohols, Organic reactions, Enantioselective synthesis, |
| Online Access: | http://hdl.handle.net/10261/211767 |
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