This work was financially supported by the Japan Society for the Promotion of Science (JSPS KAKENHI, 18K14867, 20K15956 to AK and 18H02096, 21H02069 to MA), and the Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research, BINDS) from the Japan Agency for Medical Research and Development (AMED, 19am0101084 and 21am0101084) to MA.
An asymmetric formal synthesis of trichodermamides B and C was achieved in 15 steps based on a tyrosine ester chiral-pool approach. Key features of this synthesis include stereoselective construction of a cis-1,2-oxazadecaline core by an acid-mediated tandem deprotection–intramolecular oxy-Michael reaction, oxime ether formation via an N-bromination–elimination sequence, and diene construction by a palladium-catalyzed demonomethylcarbonation.
15 The stereochemistry of allyl alcohol 21 and 22 was determined by NOESY after conversion of both compounds into the corresponding carbonate (see the Supporting Information).
16
Cha JS,
Kwon OO,
Kwon SY.
Bull. Korean Chem. Soc. 1995; 16: 1009
