Total synthesis of (-)-kendomycin exploiting a Petasis-Ferrier rearrangement/ring-closing olefin metathesis synthetic strategy.
The total synthesis of (-)-kendomycin (1), a novel macrocyclic polyketide with antibacterial and antitumor activity, was achieved in 21 steps (longest linear sequence) exploiting an effective Petasis-Ferrier union/rearrangement tactic to construct the tetrahydropyran ring, a ring-closing metathesis to generate the macrocycle, and a biomimetic quinone-methide-lactol assembly.
Smith
Amos B
AB
Department of Chemistry, Monell Chemical Senses Center, and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, PA 19104, USA. smithab@sas.upenn.edu
Mesaros
Eugen F
EF
Meyer
Emmanuel A
EA
D003500:Cyclization; D017828:Rifabutin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
C485395:kendomycin; D017828:Rifabutin