Diastereoselective addition of arylzinc reagents to a sugar aldehyde. Formal synthesis of (+)-7-epi-goniofufurone

Diastereoselective addition of arylzinc reagents to a sugar aldehyde. Formal synthesis of (+)-7-epi-goniofufurone

Wouters, Ana D.; Lüdtke, Diogo S.

Abstract:

The addition of organozinc reagents to carbonyl compounds has been a subject of intense research over the past few years. However, while dialkylzinc reagents have been the most studied compounds, the synthetic potential of arylalkylzinc reagents have been less explored, despite their interesting reactivity. In this context, we described herein our studies regarding the diastereoselective addition of arylethylzinc reagents to chiral sugar aldehydes. In addition, this methodology was applied to a formal synthesis of the styryllactone 7-epi-goniofufurone.

The addition of organozinc reagents to carbonyl compounds has been a subject of intense research over the past few years. However, while dialkylzinc reagents have been the most studied compounds, the synthetic potential of arylalkylzinc reagents have been less explored, despite their interesting reactivity. In this context, we described herein our studies regarding the diastereoselective addition of arylethylzinc reagents to chiral sugar aldehydes. In addition, this methodology was applied to a formal synthesis of the styryllactone 7-epi-goniofufurone.

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DOI: 10.5151/chempro-14bmos-R0279-1

Referências bibliográficas

• [1] 1 Paixao, M. W.; Braga, A. L.; Lüdtke, D. S. J. Braz. Chem. Soc. 2008, 19, 813.
• [2] 2 Fang, X. P.; Anderson, J. E.; Chang, X. J.; McLaughlin, J. L. J. Nat. Prod. 1991, 54, 1034.
• [3] 3 Gracza, T.; Hasenöhrl, T.; Stahl, U.; Jäger, V. Synthesis 1994, 1359.

Como citar:

Wouters, Ana D.; Lüdtke, Diogo S.; "Diastereoselective addition of arylzinc reagents to a sugar aldehyde. Formal synthesis of (+)-7-epi-goniofufurone", p-279-279. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0279-1