A facile approach to the synthesis of securinega alkaloids: stereoselective total synthesis of (−)-allonorsecurinine

Reddy, A. Sathish; Srihari, P.

doi:10.1016/j.tetlet.2012.08.088

Cited by 14 publications

(3 citation statements)

References 34 publications

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“…Srihari et al accomplished the stereoselective total synthesis of alkaloid (´)-allonorsecurinine (10) [12]. To create the stereocenter in the lactone moiety of 10, precursor 8 was readily prepared from L-proline in three steps.…”

Section: Chiral Pool: Prolinementioning

confidence: 99%

Recent Advances in Substrate-Controlled Asymmetric Induction Derived from Chiral Pool α-Amino Acids for Natural Product Synthesis

Paek

Jeong

et al. 2016

Molecules

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Chiral pool α-amino acids have been used as powerful tools for the total synthesis of structurally diverse natural products. Some common naturally occurring α-amino acids are readily available in both enantiomerically pure forms. The applications of the chiral pool in asymmetric synthesis can be categorized prudently as chiral sources, devices, and inducers. This review specifically examines recent advances in substrate-controlled asymmetric reactions induced by the chirality of α-amino acid templates in natural product synthesis research and related areas.

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Section: Chiral Pool: Prolinementioning

confidence: 99%

Recent Advances in Substrate-Controlled Asymmetric Induction Derived from Chiral Pool α-Amino Acids for Natural Product Synthesis

Paek

Jeong

et al. 2016

Molecules

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“…Given these attributes, it is unsurprising that the synthetic community has devoted significant attention to this collection of compounds,5 particularly to the challenges posed by the key shared domains within 1 – 5 . Indeed, since the inaugural total synthesis of securinine ( 1 ) by Horii in 1966,5a several other successful and highly creative approaches for forging their fused bicyclic butenolide domains have been disclosed, efforts that include selenoxide eliminations,5b,e,f,h,i,r intramolecular Wittig olefinations,5e,f,o,p,t–v ring‐closing metatheses,5j–p,s,x and alkylation of allylic bromides or mesylates 5a,h,i–m,q,t–v,x. However, most of these strategies require multiple steps to execute, typically constituting the longest (and least efficient) portion of the overall route.…”

Section: Methodsmentioning

confidence: 99%

An Efficient Approach to the Securinega Alkaloids Empowered by Cooperative N‐Heterocyclic Carbene/Lewis Acid Catalysis

et al. 2013

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Alles fügt sich zusammen: Die meisten der bisherigen Synthesen der Securinega‐Alkaloide erforderten längere Sequenzen zum Aufbau der verbrückenden Butenolid‐Domäne. Ein neuartiger Ansatz wird nun beschrieben, der mithilfe von N‐heterocyclischen Carbenen (NHCs) und Lewis‐Säuren die gesamte Domäne in einem einzigen Schritt aufbaut (siehe Schema). Die Synthese demonstriert, dass von Inalen abgeleitete Homoenolate als Nucleophile an intramolekularen Reaktionen teilnehmen können.

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“…Again, B‐ring formation of tricyclic intermediate 57 was accomplished using the sequence of Horii and co‐workers to afford norsecurinine ( 5 ) in this case. Interestingly, this sequence became increasingly popular and many groups have reported on its use in recent years …”

Section: Total Synthesis Of Securinega Alkaloidsmentioning

confidence: 97%

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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A facile approach to the synthesis of securinega alkaloids: stereoselective total synthesis of (−)-allonorsecurinine

Cited by 14 publications

References 34 publications

Recent Advances in Substrate-Controlled Asymmetric Induction Derived from Chiral Pool α-Amino Acids for Natural Product Synthesis

Recent Advances in Substrate-Controlled Asymmetric Induction Derived from Chiral Pool α-Amino Acids for Natural Product Synthesis

An Efficient Approach to the Securinega Alkaloids Empowered by Cooperative N‐Heterocyclic Carbene/Lewis Acid Catalysis

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

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