1514894-12-2Relevant articles and documents
General synthesis of the nitropyrrolin family of natural products via regioselective CO2-mediated alkyne hydration
Ding, Xiao-Bo,Furkert, Daniel P.,Brimble, Margaret A.
, p. 5418 - 5421 (2017)
The total synthesis of the 2-nitropyrrole natural products nitropyrrolins A and B and the formal synthesis of nitropyrrolin D are reported. The key 2-nitro-4-alkylpyrrole core was efficiently assembled by Sonogashira cross-coupling, with complete control of regioselectivity. An unusual carboxylative cyclization, sulfonylcarbamate formation, and base-promoted cleavage sequence enabled access to the key hydroxy ketone without affecting the protected 2-nitropyrrole unit. The total synthesis provides a general approach for preparation of the bioactive nitropyrrolin family of natural products.
Total synthesis of heronapyrrole C
Ding, Xiao-Bo,Furkert, Daniel P.,Capon, Robert J.,Brimble, Margaret A.
, p. 378 - 381 (2014/04/03)
A flexible total synthesis of the 2-nitropyrrole-derived marine natural product, (+)-heronapyrrole C, is reported. The approach is based on regioselective access to key building blocks containing the rare 4-substituted 2-nitropyrrole motif. Sharpless asymmetric epoxidation and dihydroxylation and a Shi epoxidation were used to introduce the five stereogenic centers of the bis-THF-diol side chain. The N-benzoyloxymethyl (Boz) protecting group was crucial for functionalization of the 2-nitropyrrole moiety and enabling final deprotection under mild conditions.
