- Asymmetric synthesis of the new marine epoxy lipid, (6S,7S,9S,10S)-6,9-epoxynonadec-18-ene-7,10-diol
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An efficient and stereocontrolled process is described for the preparation of (6S,7S,9S,10S)-6,9-epoxynonadec-18-ene-7,10-diol, a marine epoxy lipid isolated from the brown alga, Notheia anomala. The key 2,3,5-trisubstituted tetrahydrofuran ring was const
- Yoda, Hi Demi,Maruyama, Kazuhide,Takabe, Kunihiko
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p. 1403 - 1406
(2007/10/03)
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- β-hydroxy-γ-lactones as chiral building blocks for the enantioselective synthesis of marine natural products
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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.
- Garcia,Martin,Martin
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p. 1420 - 1428
(2007/10/03)
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- Enantiocontrolled synthesis of C-19 tetrahydrofurans isolated from the marine alga Notheia anomala
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The stereocontrolled synthesis of (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, both isolated from the brown alga Notheia anomala has been achieved. The req
- García, Celina,Soler, Marcos A.,Martín, Víctor S.
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p. 4127 - 4130
(2007/10/03)
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