ChemInform Abstract: Serratezomines A—C, New Alkaloids from Lycopodium serratum var. serratum.

Abstract

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Obscurinin A, a unique Lycopodium alkaloid possessing an 8/6/6/6/5 pentacyclic system isolated from Lycopodium obscurum L.

“…First and foremost, lycoposerramin F might be acetylated to produce intermediate i, which could undergo a Polonovski reaction to form a critical intermediate ii. 31 Next, ii might be transformed into enamine (iii), which could then undergo a cyclization reaction 32,33 to yield intermediate iv.…”

Diversity-oriented synthesis of Lycopodium alkaloids inspired by the hidden functional group pairing pattern

“…Among these alkaloids, huperzine A, with particularly potent acetylcholinesterase inhibitory activity, has been used for the treatment of neurodegenerative disorders 37 , and Serratezomine A showed cytotoxicity against murine lymphoma L1210 cells (IC 50 ¼ 9.7 mg ml À 1 ) and human epidermoid carcinoma KB cells (IC 50 410 mg ml À 1 ) (ref. 38). Because of their fascinating structures and promising biological activities, the Lycopodium alkaloids are the targets of a number of synthetic chemists engaged in total syntheses 39,40 .…”

Indoles and Indolizidines

“…Lycopodium serratum (club moss) [41] None reported [42] (Continued) substrate 14 could be derived from ketone 15 , which in turn would arise from an intramolecular oxidative coupling of the dienolate generated from indole -2malonate derivative 16 . In the forward sense, this ambitious coupling would fashion the C15 -C16 bond linkage and provide a signifi cant portion of the actinophyllic acid skeleton.…”

“…Serratezomine A 12 , (Scheme 7.31 ), a spirocyclic indolizidine, was isolated from the club moss L. serratum collected from Sapporo, Japan in 2000 [41] . 12 is a member of the structurally intriguing Lycopodium family of natural products, which has received much attention from the synthetic community [125 -130] .…”