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Asymmetric synthesis of trisubstituted oxazolidinones by the thiourea-catalyzed aldol reaction of 2-isocyanatomalonate diester.
Org Lett. 2014 Sep 19; 16(18):4758-61.OL

Abstract

A new method has been developed for the synthesis of chiral 4-carboxyl oxazolidinones by the catalytic asymmetric aldol reaction of an isocyanatomalonate diester with an aldehyde in the presence of a thiourea catalyst. The resulting chiral 4-carboxyl oxazolidinones are the equivalent of β-hydroxy-α-amino acids bearing a tri- or tetrasubstituted carbon center at their α position. With this in mind, this procedure was successfully applied to the first total synthesis of mycestericin C, which was completed in 12 steps and represents one of the shortest reported sequences for the construction of natural products of this type.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Sakamoto S
Graduate School of Pharmaceutical Sciences, Kyoto University , Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
Kazumi N
No affiliation info available
Kobayashi Y
No affiliation info available
Tsukano C
No affiliation info available
Takemoto Y
No affiliation info available

MeSH

AldehydesAmino AcidsBiological ProductsCatalysisEicosanoic AcidsMolecular StructureOxazolidinonesStereoisomerismThiourea

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

25203516

Citation

Sakamoto, Shota, et al. "Asymmetric Synthesis of Trisubstituted Oxazolidinones By the Thiourea-catalyzed Aldol Reaction of 2-isocyanatomalonate Diester." Organic Letters, vol. 16, no. 18, 2014, pp. 4758-61.
Sakamoto S, Kazumi N, Kobayashi Y, et al. Asymmetric synthesis of trisubstituted oxazolidinones by the thiourea-catalyzed aldol reaction of 2-isocyanatomalonate diester. Org Lett. 2014;16(18):4758-61.
Sakamoto, S., Kazumi, N., Kobayashi, Y., Tsukano, C., & Takemoto, Y. (2014). Asymmetric synthesis of trisubstituted oxazolidinones by the thiourea-catalyzed aldol reaction of 2-isocyanatomalonate diester. Organic Letters, 16(18), 4758-61. https://doi.org/10.1021/ol502198e
Sakamoto S, et al. Asymmetric Synthesis of Trisubstituted Oxazolidinones By the Thiourea-catalyzed Aldol Reaction of 2-isocyanatomalonate Diester. Org Lett. 2014 Sep 19;16(18):4758-61. PubMed PMID: 25203516.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric synthesis of trisubstituted oxazolidinones by the thiourea-catalyzed aldol reaction of 2-isocyanatomalonate diester. AU - Sakamoto,Shota, AU - Kazumi,Naoya, AU - Kobayashi,Yusuke, AU - Tsukano,Chihiro, AU - Takemoto,Yoshiji, Y1 - 2014/09/09/ PY - 2014/9/10/entrez PY - 2014/9/10/pubmed PY - 2015/7/15/medline SP - 4758 EP - 61 JF - Organic letters JO - Org Lett VL - 16 IS - 18 N2 - A new method has been developed for the synthesis of chiral 4-carboxyl oxazolidinones by the catalytic asymmetric aldol reaction of an isocyanatomalonate diester with an aldehyde in the presence of a thiourea catalyst. The resulting chiral 4-carboxyl oxazolidinones are the equivalent of β-hydroxy-α-amino acids bearing a tri- or tetrasubstituted carbon center at their α position. With this in mind, this procedure was successfully applied to the first total synthesis of mycestericin C, which was completed in 12 steps and represents one of the shortest reported sequences for the construction of natural products of this type. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/25203516/Asymmetric_synthesis_of_trisubstituted_oxazolidinones_by_the_thiourea_catalyzed_aldol_reaction_of_2_isocyanatomalonate_diester_ DB - PRIME DP - Unbound Medicine ER -