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Title

β-Hydroxy-γ-lactones as Chiral Building Blocks for the Enantioselective Synthesis of Marine Natural Products

AuthorsGarcía, Celia ; Martín, Tomás ; Martín, Víctor S.
KeywordsEthers
Tetrahydrofurans
Alcohols
Organic reactions
Enantioselective synthesis
Issue Date17-Jan-2001
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 66(4): 1420-1428
AbstractThe 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.
Publisher version (URL)https://doi.org/10.1021/jo0057194
URIhttp://hdl.handle.net/10261/211767
DOI10.1021/jo0057194
ISSN0022-3263
E-ISSN1520-6904
Appears in Collections:(IPNA) Artículos
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