54149-15-4Relevant academic research and scientific papers
Isolation, Structure Elucidation, and (Bio)Synthesis of Haprolid, a Cell-Type-Specific Myxobacterial Cytotoxin
Steinmetz, Heinrich,Li, Jun,Fu, Chengzhang,Zaburannyi, Nestor,Kunze, Birgitte,Harmrolfs, Kirsten,Schmitt, Viktoria,Herrmann, Jennifer,Reichenbach, Hans,H?fle, Gerhard,Kalesse, Markus,Müller, Rolf
supporting information, p. 10113 - 10117 (2016/08/16)
Myxobacteria are well-established sources for novel natural products exhibiting intriguing bioactivities. We here report on haprolid (1) isolated from Byssovorax cruenta Har1. The compound exhibits an unprecedented macrolactone comprising four modified amino acids and a polyketide fragment. As configurational assignment proved difficult, a bioinformatic analysis of the biosynthetic gene cluster was chosen to predict the configuration of each stereocenter. In-depth analysis of the corresponding biosynthetic proteins established a hybrid polyketide synthase/nonribosomal peptide synthetase origin of haprolid and allowed for stereochemical assignments. A subsequent total synthesis yielded haprolid and corroborated all predictions made. Intriguingly, haprolid showed cytotoxicity against several cell lines in the nanomolar range whereas other cells were almost unaffected by treatment with the compound.
2-Ethoxy-5-alkyl-3,4-dihydro-2H-pyrans in Organic Synthesis: A New Convenient Route to Branched δ-Ethoxy Alcohols
Menicagli, R.,Vecchiani, S.,Malanga, C.,Lardicci, L.
, p. 313 - 317 (2007/10/02)
The reaction between 2-ethoxy-5-alkyl-5,6-dichlorotetrahydropyrans and Grignard reagents has been investigated, and the overall results clearly indicate that the reaction provides a useful route to the preparation of highly branched primary, secondary, and tertiary δ-ethoxy alcohols.Experimental evidence is presented to support the occurrence of suitable epoxides as reaction intermediates that may evolve to products either through a pinacol-type isomerization and/or via a cyclic intramolecular rearrangement of a halohydrin halomagnesium salt.
