Synthesis of (+/-)-eusynstyelamide A.
The synthesis of (+/-)-eusynstyelamide A has been accomplished in six steps in 13% overall yield from 6-bromoindole, methyl glycidate, and Boc-protected agmatine. If oxygen is carefully excluded from the reaction, the key NaOH-catalyzed aldol dimerization of the alpha-ketoamide proceeded efficiently to give Boc-protected eusynstyelamide A.
Barykina
Olga V
OV
Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Snider
Barry B
BB
D002384:Catalysis; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D006842:Hydrocarbons, Brominated; D007211:Indoles; C542025:eusynstyelamide A
Chemistry. 2008;14(5):1638-47
18064625
Antimicrob Agents Chemother. 1977 Mar;11(3):411-4
324390
Bioorg Med Chem. 2005 Mar 1;13(5):1691-705
15698787
Org Biomol Chem. 2004 Jul 21;2(14):2044-9
15254632
J Nat Prod. 1994 Jun;57(6):842-5
7931370
Org Lett. 2005 Mar 3;7(5):941-3
15727480
J Am Chem Soc. 2009 Apr 1;131(12):4214-5
19317498
Org Biomol Chem. 2004 Jul 7;2(13):1864-71
15227538
Biochemistry. 1970 Jan 6;9(1):90-8
5411209
J Org Chem. 2000 Feb 11;65(3):793-800
10814012
J Nat Prod. 2009 Jun;72(6):1115-20
19505081