Studies on securinine and allosecurinine

Satoda, Isao; Murayama, Masao; Tsuji, Jiro; Yoshii, Eiichi

doi:10.1016/s0040-4039(00)70585-5

Cited by 37 publications

(21 citation statements)

References 7 publications

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“…1). 4,5 Structurally, most securinega alkaloids share a bridged tetracyclic ring system that includes a benzofuranone subunit (rings C and D) and a piperidine or a pyrrolidine ring (ring A), and the size of the latter ring defines the securinine and norsecurinine subgroups. Due to the unique structural features and interesting biological properties of the securinega alkaloids, these compounds have drawn significant attention from synthetic chemists, resulting in a number of innovative total syntheses.…”

mentioning

confidence: 99%

Total synthesis of securinega alkaloids (−)-norsecurinine, (−)-niruroidine and (−)-flueggine A

Yao

Zhao

et al. 2014

Chem. Commun.

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A consecutive synthetic strategy was developed toward the total synthesis of securinega alkaloids. (-)-Norsecurinine was concisely assembled by addition of a methoxyallene to a ketone for efficient side-chain installation. Ring-closing metathesis was also utilized as a key step. The first total synthesis of (-)-niruroidine was achieved from (-)-norsecurinine in three steps, while the route to (-)-flueggine A featured a 1,3-dipolar cycloaddition to forge the core structure.

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confidence: 99%

Total synthesis of securinega alkaloids (−)-norsecurinine, (−)-niruroidine and (−)-flueggine A

Yao

Zhao

et al. 2014

Chem. Commun.

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“…Total synthesis of the racemic natural product and chiral resolution by recrystallization with (+)‐10‐camphorsulfonic acid confirmed the structural and stereochemical assignments . Another alkaloid isolated from S. suffruticosa showed similarities to 1 and was identified as the epimer allosecurinine ( 2 ), in which the A and B rings are fused in an opposite configuration . Surprisingly, the investigation of the alkaloid content of F. virosa (synonymous with S. virosa ) yielded another stereoisomer of 1 , which was found to be its enantiomer virosecurinine ( 3 ) .…”

Section: Introductionmentioning

confidence: 76%

Securinega Alkaloids: Complex Structures, Potent Bioactivities, and Efficient Total Syntheses

Wehlauch

Gademann

2017

Asian J Org Chem

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The Securinega alkaloids feature a compact tetracyclic structural framework and can be divided into four subclasses characterized by either a bridged [2.2.2]‐ or a [3.2.1]‐bicyclic core with two homologous series in each subclass. In the last two decades, many innovative strategies to chemically access the Securinega alkaloids have been developed. This Focus Review discusses the selected structures and syntheses of representative members of the Securinega alkaloids. Ring‐closing metathesis has enabled the syntheses of securinine and norsecurinine, and different cycloaddition approaches were key to the syntheses of nirurine and virosaines A and B. Virosine A was accessed through a Vilsmeier–Haack/Mannich reaction cascade. A bio‐inspired vinylogous Mannich reaction has enabled the synthesis of allosecurinine and this strategy has been extended by an intramolecular 1,6‐addition to obtain bubbialidine and secu′amamine E. A rearrangement process of the latter two alkaloids has furnished allonorsecurinine and allosecurinine, respectively. Finally, an expanded model for the biogenesis of the Securinega alkaloid subclasses is discussed.

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“…However, its structure was not determined until 1962 when it was isolated once again and studied further 3. Along with securinine, a small amount of another compound was isolated and was found to be epimeric at the C2 position 3a. This new compound was named allosecurinine.…”

Section: Methodsmentioning

confidence: 99%

Total Synthesis of (−)‐Allosecurinine

Leduc

Kerr

2008

Angewandte Chemie

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Scheme 5. First attempts at completing the synthesis of allosecurinine. a) Hoveyda-Grubbs 2nd generation catalyst (39), THF, reflux; b) IBX, DMSO (45 %, 2 steps); c) DCC, diethylphosphonoacetic acid, CH 2 Cl 2 ; d) LiBr, NEt 3 , THF. DCC = dicyclohexyl carbodiimide. Scheme 6. Completion of the synthesis of allosecurinine. a) DCC, diethylphosphonoacetic acid, CH 2 Cl 2 (90 %); b) LiBr, NEt 3 , THF; c) Hoveyda-Grubbs 2nd generation catalyst (39), THF, reflux (40 %, 2 steps); d) DDQ, 9:1 CH 2 Cl 2 /H 2 O; e) MsCl, NEt 3 , THF (83 %, 2 steps); f) TFA/CH 2 Cl 2 then silica gel/acetone (65 %). DDQ = 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. TFA = trifluoroacetic acid. Angewandte Chemie 8065

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Studies on securinine and allosecurinine

Cited by 37 publications

References 7 publications

Total synthesis of securinega alkaloids (−)-norsecurinine, (−)-niruroidine and (−)-flueggine A

Total synthesis of securinega alkaloids (−)-norsecurinine, (−)-niruroidine and (−)-flueggine A

Securinega Alkaloids: Complex Structures, Potent Bioactivities, and Efficient Total Syntheses

Total Synthesis of (−)‐Allosecurinine

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