Improved formal total synthesis of tetrahydrometinoxocrinine

Sánchez, I. H.; Mendoza, María Teresa

doi:10.1016/s0040-4039(00)78735-1

Cited by 9 publications

(1 citation statement)

References 11 publications

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“…twelve steps into the γ-arylated butanoic acid 300 , the acid chloride derivative of which was subjected to an intramolecular Friedel–Crafts acylation reaction to afford the spiro-annulated α-tetralone 301 . Subjection of this last compound to a Schmidt reaction afforded a mixture of lactam (±)- 302 [ 77 , 78 ] and its regio-isomer with the former being elaborated over three straightforward steps into the enone (±)- 303 . This last compound is “primed” for a biomimetic C4-N5 bond forming event, and the best way to achieve this was under acidic conditions and with ethylene ketal formation following the key cyclization event to afford product (±)- 304 .…”

Section: Introductionmentioning

confidence: 99%

The Chemical Synthesis of the Crinine and Haemanthamine Alkaloids: Biologically Active and Enantiomerically-Related Systems that Serve as Vehicles for Showcasing New Methodologies for Molecular Assembly

White

Lan

et al. 2021

Molecules

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The title alkaloids, often referred to collectively as crinines, are a prominent group of structurally distinct natural products with additional members being reported on a regular basis. As such, and because of their often notable biological properties, they have attracted attention as synthetic targets since the mid-1950s. Such efforts continue unabated and more recent studies on these alkaloids have focused on using them as vehicles for showcasing the utility of new synthetic methods. This review provides a comprehensive survey of the nearly seventy-year history of these synthetic endeavors.

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Section: Introductionmentioning

confidence: 99%

The Chemical Synthesis of the Crinine and Haemanthamine Alkaloids: Biologically Active and Enantiomerically-Related Systems that Serve as Vehicles for Showcasing New Methodologies for Molecular Assembly

White

Lan

et al. 2021

Molecules

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The Krapcho Dealkoxycarbonylation Reaction of Esters with α‐Electron‐Withdrawing Substituents

Krapcho

Ciganek

2013

Organic Reactions

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The Krapcho reaction involves esters with α‐electron‐withdrawing substituents such as malonates, β‐keto esters, and α‐cyano esters, which undergo dealkoxycarbonylation on being heated in polar aprotic solvents (such as DMSO, DMF, or HMPT) in the presence of water, or in polar aprotic solvents with water in the presence of added salts (such as NaCN, NaCl, LiCl, LiI, or MgCl 2 ). This procedure avoids the use of strongly aqueous acidic and alkaline conditions and tolerates many functional and protecting groups. The chapter presents the mechanistic aspects of this procedure, which include reaction parameters such as solvents, salts, other additives, and the use of microwave irradiation. The diastereoselectivity of protonation of the enolate intermediate leading to the dealkoxycarbonylated products is discussed. Trapping of the intermediate enolate by electrophiles other than a proton is illustrated. Potential side reactions and same‐pot subsequent reactions of substrates are discussed along with functional‐group compatibility for halogens and nitrogen, oxygen, sulfur, selenium, and carbon functional groups. Several examples of applications of this methodology for the synthesis of natural products along with experimental conditions and procedures are presented. Closely related methods are discussed in the Comparison with Other Methods section. The tables, which consist of 371 pages, are grouped according to substrate structure. Selective entries for other methods (excluding classical aqueous acidic or basic methods) are included in the tabular survey for comparative purposes.

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ChemInform Abstract: IMPROVED FORMAL TOTAL SYNTHESIS OF TETRAHYDROMETINOXOCRININE

Sánchez¹,

Mendoza²

1981

Chemischer Informationsdienst

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Improved formal total synthesis of tetrahydrometinoxocrinine

Cited by 9 publications

References 11 publications

The Chemical Synthesis of the Crinine and Haemanthamine Alkaloids: Biologically Active and Enantiomerically-Related Systems that Serve as Vehicles for Showcasing New Methodologies for Molecular Assembly

The Chemical Synthesis of the Crinine and Haemanthamine Alkaloids: Biologically Active and Enantiomerically-Related Systems that Serve as Vehicles for Showcasing New Methodologies for Molecular Assembly

The Krapcho Dealkoxycarbonylation Reaction of Esters with α‐Electron‐Withdrawing Substituents

ChemInform Abstract: IMPROVED FORMAL TOTAL SYNTHESIS OF TETRAHYDROMETINOXOCRININE

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