Publication: Formal synthesis of (+)-3-epi-eupomatilone-6 and the 3,5-bis-epimer
Issued Date
2014-09-21
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ISSN
14770520
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2-s2.0-84906248897
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Mahidol University
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SCOPUS
Bibliographic Citation
Organic and Biomolecular Chemistry. Vol.12, No.35 (2014), 6885-6894
Suggested Citation
Sariya Yodwaree, Darunee Soorukram, Chutima Kuhakarn, Patoomratana Tuchinda, Vichai Reutrakul, Manat Pohmakotr Formal synthesis of (+)-3-epi-eupomatilone-6 and the 3,5-bis-epimer. Organic and Biomolecular Chemistry. Vol.12, No.35 (2014), 6885-6894. doi:10.1039/c4ob01078g Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/33224
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Title
Formal synthesis of (+)-3-epi-eupomatilone-6 and the 3,5-bis-epimer
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Abstract
The formal synthesis of (+)-3-epi-eupomatilone-6 (1) and the 3,5-bis-epimer (2) has been accomplished. The key synthetic strategy involved the stereoselective construction of (3R,4S,5R)- and (3R,4S,5S)-trisubstituted γ-butyrolactones 3 and 4 from (2R,3R)-2,3-dimethyl-4-pentenoic acid derivative 7, which was readily obtained via stereoselective conjugate addition of vinylmagnesium chloride to a chiral α,β-unsaturated N-acyl oxazolidinone (Evans' auxiliary) followed by α-methylation. This journal is © the Partner Organisations 2014.