Total synthesis of Ciliatamides A-C: stereochemical revision and the natural product-guided synthesis of unnatural analogs.
The first total synthesis of Ciliatamides A-C was completed, leading to a revision of the reported stereochemistry from (S,S) to the (R,R) enantiomers. Due to the expedited route, a library of over 50 unnatural ciliatamide analogs was also prepared.
Lewis
Jana A
JA
Department of Chemistry, Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37232, USA.
Daniels
R Nathan
RN
Lindsley
Craig W
CW
D001688:Biological Products / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D055666:Lipopeptides / Q000737:chemistry; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001688:Biological Products; D055666:Lipopeptides; D009842:Oligopeptides; C529041:ciliatamide A; C529042:ciliatamide B; C529043:ciliatamide C
J Comb Chem. 2008 May-Jun;10(3):345-54
18220367
J Med Chem. 1998 Nov 19;41(24):4885-9
9822557
Nat Rev Microbiol. 2007 Nov;5(11):873-82
17938629
J Nat Prod. 2008 Oct;71(10):1783-6
18800848
J Nat Prod. 2008 Mar;71(3):469-72
18257536
Exp Parasitol. 2006 Dec;114(4):247-52
16716301
J Comb Chem. 2003 May-Jun;5(3):322-9
12739949