The syntheses of rac-inthomycin A, (+)-inthomycin B and (+)-inthomycin C using a unified synthetic approach

Short, Tin‐Free Synthesis of All Three Inthomycins

“…The first synthesis of inthomycin A ( 1 ) in racemic form was disclosed by Whiting in 1999 with the only enantioselective synthesis of 1 being reported by Hatakeyama in 2012 who disclosed the enantioselective synthesis of inthomycins B 2 and C 3 in the same publication. In 2006 Taylor reported the first enantioselective synthesis of inthomycin B 2 followed by a report of the enantioselective synthesis of inthomycin C 3 and of racemic inthomycin A 1 in 2008 . In 2010, Ryu reported an enantioselective synthesis of inthomycin C 3 which was followed by Hale's reports on the enantioselective synthesis of 3 .…”

Stereoselective Synthesis of Dienyl-Carboxylate Building Blocks: Formal Synthesis of Inthomycin C

“…30 The conversion of 12 to Inthomycin C has been previously reported. 31 This modular assembly of substituents around dienes such as 4e allows considerable flexibility in the context of total synthesis.…”

Total Synthesis of Biologically Active Natural Products Based on Highly Selective Synthetic Methodologies

“…Compound 116 was then converted to 118 via 117 in a six-step sequence involving methylation, iodination, and diimide reduction as major transformations. Iodoalkene 118 was then subjected to Stille coupling with stannane 119 111) using Pd(PPh 3 ) 4 , CuI, and CsF in DMF at room temperature to give Z,Z,E-triene 120 in geometrically pure form. When this coupling was carried out using Pd(0) catalyst alone, some extent of isomerization of the triene system was always observed.…”