105708-56-3Relevant articles and documents
A Maillard approach to 2-formylpyrroles: Synthesis of magnolamide, lobechine and funebral
Yuen, Tsz-Ying,Eaton, Samantha E.,Woods, Tom M.,Furkert, Daniel P.,Choi, Ka Wai,Brimble, Margaret A.
, p. 1431 - 1437 (2014/03/21)
A convenient synthesis of the traditional medicine constituents magnolamide, lobechine and funebral is described. Construction of the 2-formylpyrrole core of these natural products was achieved by means of a Maillard reaction, involving condensation of the sugar surrogate, dihydropyranone 9, with the requisite primary amines. This approach offers a very direct and general route to the 2-formylpyrrole ring system. The synthesis of the 2-formylpyrrole core found in the traditional medicine constituents, magnolamide, lobechine and funebral, was constructed by a Maillard reaction, involving condensation of the sugar surrogate, dihydropyranone 9, with the requisite primary amines. This approach offers a very direct and general route to the 2-formylpyrrole ring system. Copyright
Total synthesis of (-)-funebrine via Au-catalyzed regio- and stereoselective γ-butyrolactonization of allenylsilane
Okada, Takuya,Sakaguchi, Kazuhiko,Shinada, Tetsuro,Ohfune, Yasufumi
, p. 5744 - 5746 (2011/12/15)
The stereoselective total synthesis of (-)-funebrine from 2-butyn-1-ol was described. The crucial steps in the synthesis involved the stereoselective enolate Claisen rearrangement of the (S)-α-acyloxy-α-alkynylsilane 8, the Au-catalyzed regio- and stereoselective lactonization of the allenylsilane 7, and the Paal-Knorr pyrrole condensation using an unsymmetrical 1,4-diketone 4b.
