141364-77-4Relevant articles and documents
A new synthetic route to tyromycin A and its analogue from renewable resources
Roncaglia, Fabrizio,Stevens, Christian V.,Ghelfi, Franco,Van der Steen, Marijke,Pattarozzi, Mariella,De Buyck, Laurent
, p. 1481 - 1487 (2009)
The synthesis of tyromycin A and that of the non-natural lower homologue, involving as featuring steps a transition metal catalyzed atom transfer radical cyclization and a functional rearrangement of the polyhalogenated 2-pyrrolidinones thus obtained, are
Gold-Catalyzed Cycloisomerization of Propargyl Pyruvates Enabling Unified Access to Tricladolides C and D, Chaetomellic Anhydride A, and Tyromycin A
Amin, Pathan Mosim,Su, Zhenjie,Wang, Shaozhong
, p. 15318 - 15325 (2021/11/01)
Gold-catalyzed cycloisomerization of propargyl pyruvates has been developed as a key reaction to prepare maleic anhydride-type natural products. By combining with chemoselective epoxidation of the formed γ-alkylidenebutenolides and oxidative cleavage of epoxides, the first synthesis of tricladolide D and racemic tricladolide C has been achieved in 52 and 16% overall yields with five to seven steps starting from commercially available compounds. Further catalytic hydrogenation of alkenylated maleic anhydrides derived from γ-alkylidenebutenolides produced chaetomellic anhydride A (19% yield for six steps) and tyromycin A (15% yield for six steps), which provides flexible synthetic approaches to these naturally occurring dialkylated maleic anhydrides distinct from the documented ones.
