Total synthesis and assignment of the side chain stereochemistry of LI-F04a: an antimicrobial cyclic depsipeptide.
The total synthesis of the potent antifungal and antibiotic cyclic depsipeptide LI-F04a and its side chain epimer was accomplished using macrolactonization to assemble the cyclic peptide core, followed by attachment of the 15-guanidino-3-hydroxypentadecanoyl (GHPD) side chain. The side chain was assembled by Yamaguchi-Hirao alkylation of both enantiomers of a chiral epoxide to provide a pair of enantiomeric side chains. The attachment of both these chains to the cyclic peptide allowed the absolute configuration of the side chain hydroxyl group in LI-F04a to be assigned as (R).
Cochrane
James R
JR
School of Chemistry, The University of Sydney, 2006, NSW, Australia.
McErlean
Christopher S P
CS
Jolliffe
Katrina A
KA
D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001407:Bacillus / Q000737:chemistry*; D001426:Bacterial Proteins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D013237:Stereoisomerism
D000890:Anti-Infective Agents; D000935:Antifungal Agents; D001426:Bacterial Proteins; D047630:Depsipeptides; C553073:LI-F04a peptide, Bacillus