Abstract
The palhinine family of Lycopodium alkaloids were first reported in 2010, which feature an intriguing isotwistane carbon cage and a nine-membered azonane ring. It is noteworthy that the tetracyclic 5/6/6/9 skeleton was unprecedented in Lycopodium alkaloids before their seminal discovery. Over the past decade, extensive synthetic efforts stemming from seven research groups have resulted in two racemic total syntheses to date. This review article takes the opportunity to survey these efforts and achievements so as to promote further research towards the asymmetric total synthesis of palhinine alkaloids.
Highlights
Lycopodium alkaloids [1] are a vast group of structurally related natural products isolated from the plants of the genus Lycopodium
Palhinines A–C [3,4] possess a 5/6/6/9 tetracyclic carbon ring system with different oxidation positions and configurations, while isopalhinine A [4] and palhinine D [6] have a more congested 5/6/6/6/7 aza-pentacyclic skeleton owing to the hemiaminalization of the carbonyl group and the secondary amine
This review reviewsummarizes summarizesallall reported studies toward the total synthesis the palhinine alkaloids since their isolation in 2010. in During decade its discovery, diverse synthetic family alkaloids since their isolation
Summary
Lycopodium alkaloids [1] are a vast group of structurally related natural products isolated from the plants of the genus Lycopodium. They feature distinctive polyfused-bridged skeletons and impressive biological activities, including cytotoxicity, antimicrobial activity, anti-HIV-1 activity, enhanced mRNA expression for nerve growth factor, inhibition of pro-inflammatory factors, and inhibition of acetylcholinesterase (AChE). The isotwistane skeleton was thought to originate biosynthetically from fawcettimine, a well-known Lycopodium alkaloid, through a new bridged connection between C-4 and C-16 [4] Due to their scarcity in nature, palhinine alkaloids were reported to only be examined in limited bioassays, which showed no obvious activities.
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