Total syntheses of the lycopodium alkaloids (.+-.)-fawcettimine and (.+-.)-8-deoxyserratinine.
نویسندگان
چکیده
منابع مشابه
Natural Product Synthesis
The Lycopodium alkaloids are a family of structurally complex natural products, which have provoked long-term interests in their total syntheses because of their unique and fascinating architectures and potential biological activities. In particular, fawcettimine-type Lycopodium alkaloids, such as fawcettimine (1) and fawcettidine (2) (Scheme 1), have attracted broad attention from the syntheti...
متن کاملThe Genus Diphasiastrum and Its Lycopodium Alkaloids.
The genus Diphasiastrum includes at least 23 species distributed primarily across the northern temperate and subarctic areas of the world. These plants produce an array of lycopodium alkaloids, and some species such as Diphasiastrum complanatum have been used in traditional medicine for ages for various conditions. Hybridization is common in this group of plants and they have always been a chal...
متن کاملTotal synthesis of (+)-fawcettimine.
The fawcettimine class of Lycopodium alkaloids consists of over 60 natural products. Typically, these tetracyclic compounds contain a single quaternary carbon center and are derived biosynthetically from the lycopodane core through an oxidative rearrangement reaction. In 1959, the first member of this class, fawcettimine (1), was isolated by Burnell in the Blue Mountain Range of Jamaica. Inubus...
متن کاملCollective synthesis of Lycopodium alkaloids and tautomer locking strategy for the total synthesis of (-)-lycojapodine A.
The collective total synthesis of Lycopodium alkaloids (+)-fawcettimine (1), (+)-fawcettidine (2), (+)-alopecuridine (4), (-)-lycojapodine A (6), and (-)-8-deoxyserratinine (7) has been accomplished from a common precursor (15) based on a highly concise route inspired by the proposed biosynthesis of the fawcettimine- and serratinine-type alkaloids. An intramolecular C-alkylation enabled efficie...
متن کاملLannotinidines H-J, new Lycopodium alkaloids from Lycopodium annotinum.
Three new Lycopodium alkaloids, lannotinidines H-J (1-3), were isolated from the club moss Lycopodium annotinum. The structures and relative stereochemistry of 1-3 were elucidated on the basis of spectroscopic data and the absolute stereochemistry of 2 was assigned by chemical correlation. Lannotinidine H (1) is the first Lycopodium alkaloid possessing a lycopodane skeleton with an additional C...
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ژورنال
عنوان ژورنال: Chemical and Pharmaceutical Bulletin
سال: 1980
ISSN: 0009-2363,1347-5223
DOI: 10.1248/cpb.28.2394