Synthesis of nodulisporic acid 2' '-oxazoles and 2' '-thiazoles.
[reaction--see text] The semisynthetic conversion of nodulisporic acid A (1) into a set of three heterocyclic side chain derivatives provided compounds, highlighted by 6, with an improved spectrum of ectoparasiticidal activity and pharmacokinetic profile relative to the natural product.
Berger
R
R
Merck Research Laboratories, Merck & Co., Inc., Rahway, New Jersey 07065, USA.
Shoop
W L
WL
Pivnichny
J V
JV
Warmke
L M
LM
Zakson-Aiken
M
M
Owens
K A
KA
deMontigny
P
P
Schmatz
D M
DM
Wyvratt
M J
MJ
Fisher
M H
MH
Meinke
P T
PT
Colletti
S L
SL
D000818:Animals; D007211:Indoles / Q000138:chemical synthesis*; D007306:Insecticides / Q000138:chemical synthesis*; D010080:Oxazoles / Q000138:chemical synthesis*; D005423:Siphonaptera; D013844:Thiazoles / Q000138:chemical synthesis*; D013987:Ticks
D007211:Indoles; D007306:Insecticides; D010080:Oxazoles; D013844:Thiazoles; C110703:nodulisporic acid A