Total synthesis of (-)-callystatin A.
[reaction: see text] A convergent enantioselective synthesis of the natural product (-)-callystatin A (1) is described. Key features of the synthesis include a lipase-mediated kinetic resolution to install the C5 lactone stereochemistry, a hydrozirconation-based approach to the C8-C9 trisubstituted (Z)-olefin, and a stereoselective cross-coupling of a vinyl dibromide to install the C14-C15 trisubstituted (E)-olefin.
Langille
Neil F
NF
Department of Chemistry and Center for Chemical Methodology and Library Development, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
Panek
James S
JS
D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D000818:Animals; D002384:Catalysis; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism; D014001:Tin / Q000737:chemistry
D000475:Alkenes; D005231:Fatty Acids, Unsaturated; C421091:callystatin A; D014001:Tin