Biomimetic total synthesis of malbrancheamide and malbrancheamide B.
The biomimetic total syntheses of both malbrancheamide and malbrancheamide B are reported. The synthesis of the two monochloro species enabled the structure of malbrancheamide B to be unambiguously assigned. The syntheses each feature an intramolecular Diels-Alder reaction of a 5-hydroxypyrazin-2(1H)-one to construct the bicyclo[2.2.2]diazaoctane core, which has also been proposed as the biosynthetic route to these compounds.
Miller
Kenneth A
KA
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523-1872, USA.
Welch
Timothy R
TR
Greshock
Thomas J
TJ
Ding
Yousong
Y
Sherman
David H
DH
Williams
Robert M
RM
D000577:Amides / Q000737:chemistry; D032701:Biomimetics; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D026121:Indole Alkaloids; D015394:Molecular Structure; D010084:Oxidation-Reduction
D000577:Amides; D006576:Heterocyclic Compounds, 4 or More Rings; D026121:Indole Alkaloids; C529354:malbrancheamide