Stereoselective synthesis of the C1-C11 and C12-C34 fragments of mycalolide A.
A convergent synthesis of the C1-C11 and C12-C34 fragments of mycalolide A is described. Synthetic highlights include a highly E-selective cross-metathesis between a vinyl-functionalized bis-oxazole unit and a polypropionate side chain to introduce the C19-C20 double bond and an enzymatic desymmetrization of a meso-diol in addition to five stereoselective allylations/crotylations to control the 11 stereogenic centers present in the natural product.
Hoffman
Thomas J
TJ
Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
Kolleth
Amandine
A
Rigby
James H
JH
Arseniyadis
Stellios
S
Cossy
Janine
J
D000818:Animals; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008387:Marine Toxins; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
D018942:Macrolides; D008387:Marine Toxins; D010080:Oxazoles; C553072:mycalolide A