98873-83-7Relevant articles and documents
Total synthesis of (+)-trienomycins A and F via C-C bond-forming hydrogenation and transfer hydrogenation
Del Valle, David J.,Krische, Michael J.
, p. 10986 - 10989 (2013/08/23)
The triene-containing C17-benzene ansamycins trienomycins A and F were prepared in 16 steps (longest linear sequence, LLS) and 28 total steps. The C11-C13 stereotriad was generated via enantioselective Ru-catalyzed alcohol CH syn crotylation followed by chelation-controlled carbonyl dienylation. Enantioselective Rh-catalyzed acetylene-aldehyde reductive coupling mediated by gaseous H2 was used to form a diene that ultimately was subjected to diene-diene ring closing metathesis to form the macrocycle. The present approach is 14 steps shorter (LLS) than the prior syntheses of trienomycins A and F, and 8 steps shorter than any prior synthesis of a triene-containing C17-benzene ansamycin.
ISOLATION AND STRUCTURE DETERMINATION OF (+)-TRIENOMYCIN F. AN ENDGAME SYNTHETIC STRATEGY FOR THE TRIENOMYCIN FAMILY OF ANTITUMOR ANTIBIOTICS
Smith, Amos B.,Wood, John L.,Gould, Alexandra E.,Omura, Satoshi,Komiyama, Kanki
, p. 1627 - 1630 (2007/10/02)
A new trienomycin antibiotic, (+)-trienomycin F (4), has been isolated and characterized.The structure was elucidated via spectroscopic comparison with semisynthetic 4 prepared from (+)-trienomycinol (5).The latter sequence implemented an endgame syntheti