Total synthesis and complete stereochemical assignment of heronapyrroles A and B

Marine Pyrrole Alkaloids

“…In 2015, the Morimoto group published the total synthesis of the remaining (+)-heronapyrroles A ( 111 ) and B ( 112 ) [ 121 ]. Taking into account the reported syntheses of (−)-heronapyrrole C ( ent - 113b ) by Stark (2012) and (+)-heronapyrrole C ( 113a ) by Brimble (2014) together with the biogenetic relationship of heronapyrroles A–C ( 111 – 113 ), a stereochemical reassignment of pyrroles 111 and 112 was proposed.…”

“…This rare class of nitropyrroles has attracted some attention from synthetic chemists in recent years. Not least because of previous synthetic work and the promising effects against Gram-positive bacteria, nitropyrroles may represent interesting targets for further drug design [ 115 , 117 , 118 , 120 , 121 , 122 , 123 ].…”

“…In both cases, the absolute configuration was determined by the Mosher method which confirmed the proposed structure. As a consequence, the initially proposed stereochemistries for heronapyrroles A (111) and B (112) from the Stark laboratory in 2012 were reassigned [121]. This rare class of nitropyrroles has attracted some attention from synthetic chemists in recent years.…”

Marine natural products

“…131,132 A new route to isoquinolines was developed for the synthesis of mansouramycin 133,134 and a total synthesis and full stereochemical assignments have been completed for heronapyrroles A 168 and B 169. 135,136 A further synthesis of bacillamide B 137 has reconrmed the absolute conguration as (S) and that the specic optical rotation is negative. 138 The unusual anthracycline marmoycin 139 has been successfully synthesised and uorescent microscopy studies indicated that it accumulates in the lysosomes and not the cell nucleus.…”

Recent progress in the total synthesis of pyrrole-containing natural products (2011–2020)

“…Their promising biological activity against MRSA strains and colon cancer cell lines make them attractive targets for drug development. [32][33][34] Gulder et al 35 Morimoto et al 38 described a total synthesis of (+)heronapyrrole A 51 in 2015 (Scheme 7). Their strategy commenced with the preparation of epoxy bromide 54 from known (15S)-diol 52 38 through a five step sequence, including a chemoselective bromoetherification to form the tetrahydrofuran ring as a protecting group for the central trisubstituted alkene.…”