1514894-42-8Relevant articles and documents
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.