Towards Allopumiliotoxins: A Concise Synthesis of the Indolizidine Core

Vijaykumar, B.V.D.; Pitchakuntla, Mallesham; Chandrasekhar, Srivari

doi:10.1002/ejoc.201101430

Cited by 10 publications

(1 citation statement)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Indolizidine class of alkaloids, allopumiliotoxins ( 92.5 ) are 7‐hydroxy congeners of pumiliotoxins, isolated from the Dendrobatidae family of frogs, possess substituted 5,6‐fused azabicyclic core (indolizidine frame), an ( E )‐geometric exocyclic olefin. Vijaykumar et al [103] . isolated the Evans syn ‐aldol product 92.2 as the major diastereomer (dr >98 : 2) in 78% yield from Crimmins’ aldol addition of the Ti‐enolate of N ‐propionyl thiazolidinethione 70.2 to aldehyde 92.1 in the presence of TiCl 4 , DIPEA, and NMP.…”

Section: Thiazolidinethione Chiral Auxiliaries In Asymmetric Synthesismentioning

confidence: 99%

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

2021

View full text Add to dashboard Cite

Nature is incessantly affianced to construct bioactive and structurally intriguing compounds with magnificent three‐dimensional frameworks in the Universe. The inadequacy of these naturally occurring precious compounds prompted several minds of chemists to synthesise them in a laboratory for a thorough evaluation of their medicinal and clinical properties via a structure‐activity relationship study. Finding an optimised methodology to synthesise chiral natural products has always been challenging in synthetic organic chemistry, particularly the formation of asymmetric carbon‐carbon bonds adhering to the existing stereochemistry. In this context, chiral auxiliaries have proven to be effective tools for inducing chirality during the synthesis of chiral molecules. In fact, the chiral auxiliary will allow us to control the synthesis of many enantiomerically pure isomers in natural product synthesis. In this area, the significant contribution of the Evans’ chiral auxiliary in TiCl4‐mediated asymmetric aldol reactions to the installation of known configurations in organic synthetic chemistry motivated us to compile an exhaustive and systematic summary of the relevant research findings published in the last two decades.

show abstract

Section: Thiazolidinethione Chiral Auxiliaries In Asymmetric Synthesismentioning

confidence: 99%

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

2021

View full text Add to dashboard Cite

show abstract

Studies on Pumiliotoxin A Alkaloids: An Approach to Preparing the Indolizidinic Core by Intramolecular Diastereoselective N‐Heterocyclic Carbene Catalyzed Benzoin Reaction

2016

View full text Add to dashboard Cite

show abstract

Synthesis of 1‐Deoxy‐8,8a–di–epi–castanospermine, 1‐Deoxy‐6,7,8a–tri–epi–castanospermine and Formal Synthesis of Pumilotoxin 251D

Chacko

Ramapanicker

2016

ChemistrySelect

View full text Add to dashboard Cite

An efficient synthesis of 1‐deoxy‐8,8a‐di‐epi‐castanospermine and 1‐deoxy‐6,7,8a‐tri‐epi‐castanospermine through the use of proline‐catalyzed asymmetric α‐aminoxylation of an N‐Boc derivative of L‐homoprolinal is reported. The configuration of the proline catalyst used for the asymmetric aminoxylation step ultimately controls the absolute configuration of three adjacent stereogenic centers in the final products. The method is also used to achieve a formal synthesis of Pumilotoxin 251D.

show abstract

Towards Allopumiliotoxins: A Concise Synthesis of the Indolizidine Core

Abstract: The common bicyclic indolizidine core present in several allopumiliotoxins was synthesized by the sequential use of a Crimmins' aldol reaction, an SOCl2‐mediated SNi displacement, and an intramolecular nucleophilic acyl substitution (INAS) as the key transformations.

Cited by 10 publications

References 38 publications

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

Studies on Pumiliotoxin A Alkaloids: An Approach to Preparing the Indolizidinic Core by Intramolecular Diastereoselective N‐Heterocyclic Carbene Catalyzed Benzoin Reaction

Synthesis of 1‐Deoxy‐8,8a–di–epi–castanospermine, 1‐Deoxy‐6,7,8a–tri–epi–castanospermine and Formal Synthesis of Pumilotoxin 251D

Contact Info

Product

Resources

About

Towards Allopumiliotoxins: A Concise Synthesis of the Indolizidine Core

Abstract: The common bicyclic indolizidine core present in several allopumiliotoxins was synthesized by the sequential use of a Crimmins' aldol reaction, an SOCl2‐mediated SNi displacement, and an intramolecular nucleophilic acyl substitution (INAS) as the key transformations.

Cited by 10 publications

References 38 publications

TiCl4‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

TiCl4‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

Studies on Pumiliotoxin A Alkaloids: An Approach to Preparing the Indolizidinic Core by Intramolecular Dia­stereoselective N‐Heterocyclic Carbene Catalyzed Benzoin Reaction

Synthesis of 1‐Deoxy‐8,8a–di–epi–castanospermine, 1‐Deoxy‐6,7,8a–tri–epi–castanospermine and Formal Synthesis of Pumilotoxin 251D

Contact Info

Product

Resources

About

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

Studies on Pumiliotoxin A Alkaloids: An Approach to Preparing the Indolizidinic Core by Intramolecular Diastereoselective N‐Heterocyclic Carbene Catalyzed Benzoin Reaction