Allostreptopyrroles A–E, β-alkylpyrrole derivatives from an actinomycete Allostreptomyces sp. RD068384

• Marwa Elsbaey,
• Naoya Oku,
• Mohamed S. A. Abdel-Mottaleb and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2024, 20, 1981–1987, doi:10.3762/bjoc.20.174

• 2-nitro congeners, nitropyrrolins [14] and heronapyrroles [15], bearing a farnesyl chain at the C4 position. Pyrroloterpenes are proposed to be of mixed biogenesis, elaborated from an aromatic pyrrole moiety and a terpenoid chain [15]. Prodigiosin, a major metabolite of Serratia, is another example

Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery

• Jens Schmidt,
• Zeinab Khalil,
• Robert J. Capon and
• Christian B. W. Stark

Beilstein J. Org. Chem. 2014, 10, 1228–1232, doi:10.3762/bjoc.10.121

• /bjoc.10.121 Abstract The heronapyrroles A–C have first been isolated from a marine-derived Streptomyces sp. (CMB-0423) in 2010. Structurally, these natural products feature an unusual nitropyrrole system to which a partially oxidized farnesyl chain is attached. The varying degree of oxidation of the

• sesquiterpenyl subunit in heronapyrroles A–C provoked the hypothesis that there might exist other hitherto unidentified metabolites. On biosynthetic grounds a mono-tetrahydrofuran-diol named heronapyrrole D appeared a possible candidate. We here describe a short asymmetric synthesis of heronapyrrole D, its

• : biomimetic synthesis; biosynthesis; heronapyrroles; microbial biodiscovery; natural products; nitropyrroloterpenes; Introduction Heronapyrroles A–C (Figure 1) were first reported in 2010 by Capon et al. from a marine-derived Streptomyces sp. (CMB-M0423) obtained from a shallow water sand sample collected