- Asymmetric, stereocontrolled total synthesis of paraherquamide A
-
Paraherquamide A (1), a potent anthelmintic agent, isolated from various Penicillium species with activity against ivermectin-resistant intestinal parasites, has been synthesized. The synthesis of a key intermediate, the α-isoprenylated, β-substituted hydroxyproline derivative, exploited a highly diastereoselective intramolecular S(N)2' cyclization as a key step. This procedure is the first asymmetric, stereocontrolled, total synthesis of 1.
- Williams, Robert M.,Cao, Jeffrey,Tsujishima, Hidekazu
-
-
Read Online
- Asymmetric, stereocontrolled total synthesis of paraherquamide A
-
The first total synthesis of paraherquamide A, a potent anthelmintic agent isolated from various Penicillium sp. with promising activity against drug-resistant intestinal parasites, is reported. Key steps in this asymmetric, stereocontrolled total synthesis include a new enantioselective synthesis of (α-alkylated-β-hydroxyproline derivatives to access the substituted proline nucleus and a highly diastereoselective intramolecular S N2′ cyclization to generate the core bicyclo[2.2.2]diazaoctane ring system.
- Williams, Robert M.,Cao, Jianhua,Tsujishima, Hidekazu,Cox, Rhona J.
-
p. 12172 - 12178
(2007/10/03)
-
- Conversion of marcfortine A to paraherquamide A via paraherquamide B. The first formal synthesis of paraherquamide A
-
The paraherquamides and marcfortines represent a novel class of anthelmintics. The sole structural difference between paraherquamide A and marcfortine A occurs in ring G. We synthesized paraherquamide B from marcfortine A in six steps. Paraherquamide A was then prepared from paraherquamide B in seven steps. This represents the first formal synthesis of paraherquamide A.
- Lee, Byung H.,Clothier, Michael F.
-
p. 1795 - 1798
(2007/10/03)
-