Formyl group activation of a bromopyrrole ester in Suzuki cross-coupling reactions: application to a formal synthesis of Polycitone A聽and B and Polycitrin A

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• 作者：John T. Gupton ; ^{jgupton@richmond.edu" class="auth_mail} ; Nakul Telang ; Michael Wormald ; Kristin Lescalleet ; Jon Patteson ; Will Curry ; Andrew Harrison ; Megan Hoerrner ; John Sobieski ; Michael Kimmel ; Emily Kluball ; Thomas Perry
• 关键词：Suzuki cross-coupling ; Pyrrole ; Vilsmeier formylation ; Marine natural products
• 刊名：Tetrahedron
• 出版年：29 April, 2014
• 年：2014
• 卷：70
• 期：17
• 页码：2738-2745
• 全文大小：444 K

文摘

A new pyrrole building block is described, which allows for the regiospecific synthesis of 2,3,5-trisubstituted pyrroles and 2,3,4,5-tetrasubstituted pyrroles. Optimization studies are presented for the preparation of the pyrrole building block along with the evaluation of various cross-coupling conditions and cross-coupling agents. A short, formal synthesis of the natural products Polycitone A, Polycitone B, and Polycitrin A from the pyrrole building block is also described.