1036355-92-6Relevant articles and documents
The application of formyl group activation of bromopyrrole esters to formal syntheses of lycogarubin C, permethyl storniamide A and lamellarin G trimethyl ether
Gupton, John T.,Telang, Nakul,Patteson, Jon,Lescalleet, Kristin,Yeudall, Scott,Sobieski, John,Harrison, Andrew,Curry, Will
, p. 9759 - 9767 (2015/01/09)
Lycogarubin C, permethyl storniamide A, and lamellarin G trimethyl ether are pyrrole containing, natural products, which exhibit interesting biological properties. Such properties include anti-tumor activity on a variety of cancer cell lines including those that confer drug resistance, inhibition of HIV integrase, and vascular disrupting activity. We now describe the use of methyl and ethyl 3-bromo-2-formylpyrrole-5-carboxylate as building blocks for the formal synthesis of these three highly functionalized, bioactive pyrroles. These new building blocks will now provide ready access to the natural products and many novel analogs due to the ability to easily modify positions 2,3,4, and 5 of the pyrrole core.
The application of vinylogous iminium salt derivatives and microwave accelerated Vilsmeier-Haack reactions to efficient relay syntheses of the polycitone and storniamide natural products
Gupton, John T.,Banner, Edith J.,Sartin, Melissa D.,Coppock, Matthew B.,Hempel, Jonathan E.,Kharlamova, Anastasia,Fisher, Daniel C.,Giglio, Ben C.,Smith, Kristin L.,Keough, Matt J.,Smith, Timothy M.,Kanters, Rene P.F.,Dominey, Raymond N.,Sikorski, James A.
, p. 5246 - 5253 (2008/09/21)
Studies directed at the synthesis of polycitone and storniamide natural products via vinylogous iminium salts and microwave accelerated Vilsmeier-Haack formylations are described. The successful strategy relies on the formation of a 2,4-disubstituted pyrrole or a 2,3,4-trisubstituted pyrrole from a vinamidinium salt or vinamidinium salt derivative followed by formylation at the 5-position of the pyrrole. Subsequent transformations of the selectively formylated pyrroles lead to efficient and regiocontrolled relay syntheses of the respective pyrrole containing natural products.
