Synthesis Of Lycopodium Alkaloids Research Articles

Studies on the Synthesis of Phlegmarine-Type Lycopodium Alkaloids: Enantioselective Synthesis of (-)-Cermizine B, (+)-Serratezomine E, and (+)-Luciduline.

The synthesis of the Lycopodium alkaloids, (-)-cermizine B, (+)-serratezomine E, and (+)-luciduline using phenylglycinol-derived tricyclic lactams as chiral scaffolds, is reported. The requisite lactams are prepared by a cyclocondensation reaction between ( R)- or ( S)-phenylglycinol and the substituted δ-keto ester 11, easily accessible from ( R)-pulegone. The factors governing the stereoselectivity of these cyclocondensation reactions are discussed. Key steps of the synthesis from the stereochemical standpoint are the stereoselective elaboration of the allyl substituent to the ( S)-2-(piperidyl)methyl moiety and the stereoselective removal of the chiral inductor to give a cis-decahydroquinoline.

リコポジウムアルカロイドの合成研究

リコポジウムアルカロイドの合成研究

Advances in the Collective Synthesis of Lycopodium Alkaloids

Advances in the Collective Synthesis of <i>Lycopodium</i> Alkaloids

Synthesis of Lycopodium Alkaloids Containing Seven-Membered Rings

Synthesis of Lycopodium Alkaloids Containing Seven-Membered Rings

ChemInform Abstract: Lycopodium Alkaloids — Synthetic Highlights and Recent Developments

AbstractReview: 284 refs.

Asymmetric Total Synthesis of (+)-Luciduline: Toward a General Approach to Related Lycopodium Alkaloids

As part of a research program directed toward the synthesis of Lycopodium alkaloids, a multigram scale asymmetric synthesis of intermediate 11 was achieved in 11 steps from pyridine (17). In addition to our alkene metathesis strategy, a key feature of this synthetic approach consists of a Fukuyama's Diels-Alder cycloaddition between 1,2-dihydropyridine and acrolein using MacMillan's catalyst (18) on a 50 g scale. This led to a 12-step catalytic asymmetric synthesis of (+)-luciduline (1). A broader subset of Lycopodium alkaloids could also be obtained, as demonstrated by the derivatization of 11 into advanced intermediates for the synthesis of some of these natural products.

An intramolecular Diels-Alder/retro-Mannich approach to the cis-perhydroquinoline ring system. Model studies toward the synthesis of Lycopodium alkaloids

Model studies toward the preparation of cis-decahydroquinoline derivatives using an IMDA/retro-Mannich strategy were carried out. Tricyclic amino ester 13, prepared via an IMDA reaction of 1,2-dihydropyridine 11, was ring-opened on treatment with excess LDA. Trapping the intermediate dianion 17 with TMSCl gave the polysilylated derivatives 18. Subsequent N-acylation with benzyl chloroformate provided ene carbamate 19, which on catalytic hydrogenation gave the desired decahydroquinoline 21

Synthesis of lycopodium alkaloids. II. Development of stereospecific synthetic methods

Synthesis of lycopodium alkaloids. II. Development of stereospecific synthetic methods

Transannular hydride shifts. An application to the synthesis of Lycopodium alkaloids

Transannular hydride shifts. An application to the synthesis of Lycopodium alkaloids