Journal
CHEMICAL & PHARMACEUTICAL BULLETIN
Volume 50, Issue 6, Pages 711-740Publisher
PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/cpb.50.711
Keywords
paraherquamide; marcfortine; brevianamide; asperparaline; biological Diels-Alder; asymmetric synthesis; biosynthesis
Funding
- NCI NIH HHS [CA 70375] Funding Source: Medline
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The syntheses and biosyntheses of the paraherquamide and brevianamide families of prenylated indole-derived alkaloids are reviewed. It has been proposed that the unique bicyclo[2.2.2]diazaoctan ring system that is common to this family of natural products, arises by a biological intramolecular Diels-Alder cycloaddition reaction. Both synthetic approaches and total syntheses of several members of this family of natural products are reviewed. The biosynthesis of these alkaloids has also constituted an active area of research and the current state of knowledge on the biosynthesis of these natural products are reviewed.
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