Synthesis of Proteasome Inhibitor Omuralide Featuring Stereocontrolled Ugi Reaction and Novel Convertible Isocyanide

• Gilley Cynthia B.

  Department of Chemistry and Biochemistry, University of California

• Buller Matthew J.

  Department of Chemistry and Biochemistry, University of California

• Kobayashi Yoshihisa

  Department of Chemistry and Biochemistry, University of California

抄録

Stereocontrolled formal total synthesis of proteasome inhibitor omuralide is described. This is featured by the application of Ugi 4–center 3–component condensation reaction to prepare a highly functionalized pyroglutamic acid. To this end, a novel convertible isocyanide was developed, which is readily available by preparative synthesis from nitrotoluene. The hydrolysis of the sterically hindered C–terminal amide derived from the isocyanide was facilitated by the conversion to N–acylindole. By careful design of the γ–ketoacid precursor, a substrate–controlled diastereoselective Ugi reaction was successfully accomplished. Also, several highly functionalized pyroglutamic acid amides were prepared with high diastereoselectivity.

収録刊行物

• 有機合成化学協会誌

  有機合成化学協会誌 67 (11), 1183-1193, 2009

  公益社団法人 有機合成化学協会

キーワード

• Organic Chemistry

詳細情報

• CRID: 1390001205312226944
• NII論文ID: 10026866938
• NII書誌ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.67.1183
• COI: 1:CAS:528:DC%2BD1MXhsVGgtrjK
• ISSN: 18836526
• ISSN: 00379980
• NDL書誌ID: 10493471
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I10493471
• 本文言語コード: en
• データソース種別:
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