Isolierung und Strukturaufklärung von Chaetocin

Abstract

The structure and absolute configuration of Chaetocin, a metabolite of the fungus Chaetomium minzltum with antibacterial and cytostatic activity has been elucidated by chemical and X-ray methods.

Structure, Bioactivity and Synthesis of Natural Products with Hexahydropyrrolo[2,3‐b]indole

“…These include the neurokinin antagonists (+)-WIN64 821 (38) and (+)-WIN64 745 (39), both isolated from a strain of Aspergillus sp. ; [64][65][66] (À)-ditryptophenaline (40), obtained from Aspergillus flavus; [67] the antiviral agent (+)-asperdimin (41), isolated from extracts of Aspergillus niger; [68] chaetocin (42), isolated from the fermentation broth of Chaetomium minutum; [69] verticillins A (43), B, and C, obtained from Verticillium sp., exhibit antimicrobial activity against Gram-positive bacteria and potent antitumor activity in HeLa cell lines; [70][71][72] gliocladines A (44) and B (45); [24] 11,11'-dideoxyverticillin A and 11'-deoxyverticillin A; [24,73] melinacidins; [74][75][76] Sch52 900 and Sch52 901; [24] and some leptosins A (46), B (47), and C (48). [23] Leptosins C and F, isolated from the marine fungus Leptoshaeria sp., have inhibitory activity against topoisomerases I and II [77] (Scheme 2).…”

Epidithiodioxopiperazines. occurrence, synthesis and biogenesis

“…It was isolated from Chaetomium minutum in 1970. 82,83 Fifteen years passed before the penta- and hexasulfide homologs chaetocin B and C ( 78 and 79 ) were isolated from Chaetomium spp., along with the novel octasulfide chetracin A ( 80 ). 84 In 2012, several related metabolites were isolated from Oidiodendron truncatum , including the tetra-, penta- and hexasulfide homologs melinacidin IV, chetracins B and C ( 82 , 83 , and 84 ), and the dethiotetra(methylthio) derivative chetracin D ( 85 ).…”

Total Synthesis of (+)-11,11'-Dideoxyverticillin A

“…1) (1) is a member of the epidithiodiketopiperazine alkaloids, a large family of natural products that has received significant attention from the scientific community for its rich biological activity and complex molecular architecture (2–7). The dimeric subset of alkaloids to which the title compound belongs has been known for nearly four decades with the isolation of (+)-chaetocin A ( 2 , 8) and (+)-verticillin A ( 3 , 9). Reflective of the daunting challenges posed by molecular structures replete with sterically congested stereogenic centers, and highly acid-, base-, and redoxsensitive functional groupings (5), no dimeric epidithiodiketopiperazine alkaloid has yet succumbed to total synthesis.…”