The boronic acid Mannich reaction in alkaloid synthesis

Pyne, Stephen G.; Davis, Andrew R.; Ritthiwigrom, Thunwadee; Au, Christopher W. G.; Savaspun, Kongdech; Wotherspoon, Matthew

doi:10.1351/pac-con-12-07-05

Cited by 9 publications

(4 citation statements)

References 25 publications

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“…Pyne and coworkers reported the PR-based synthesis of diverse polyhydroxylated alkaloids, 197 among which was a 10-step total synthesis of calystegine B4 alkaloids. 198 Different from a previous zinc-mediated tandem reaction with a RCM–hydroboration–oxidation sequence, 199 a PR of benzylamine, ( E )-styrylboronic acid, and (−)- d -lyxose was used for the synthesis of aminotetrol 285 , which was converted to the RCM substrate 286 to give oxidation–RCM or RCM–oxidation product 287 , and the remaining steps of deprotection and cyclization gave calystegine B4 288 with an overall yield of 3.4 or 4.7% (Scheme 75).…”

Section: Application In the Synthesis Of Natural Productsmentioning

confidence: 99%

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Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

2019

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The Petasis boron–Mannich reaction, simply referred to as the Petasis reaction, is a powerful multicomponent coupling reaction of a boronic acid, an amine, and a carbonyl derivative. Highly functionalized amines with multiple stereogenic centers can be efficiently accessed via the Petasis reaction with high levels of both diastereoselectivity and enantioselectivity. By drawing attention to examples reported in the past 8 years, this Review demonstrates the breadth of the reactivity and synthetic applications of Petasis reactions in several frontiers: the expansion of the substrate scope in the classic three-component process; nonclassic Petasis reactions with additional components; Petasis-type reactions with noncanonical substrates, mechanism, and products; new asymmetric versions assisted by chiral catalysts; combinations with a secondary or tertiary transformation in a cascade- or sequence-specific manner to access structurally complex, natural-product-like heterocycles; and the synthesis of polyhydroxy alkaloids and biologically interesting molecules.

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Section: Application In the Synthesis Of Natural Productsmentioning

confidence: 99%

Section: Polyhydroxy Alkaloidsmentioning

confidence: 99%

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

2019

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“…Many noval MCRs [57][58][59][60][61][62][63][64][65][66][67][68][69][70][71][72][73] have meanwhile become part of the range of syntheses, e.g. boron-mediated [62,66], photo-induced [67] and carbenebased MCRs [72] such as N-heterocyclic carbenes (NHCs). They all increase the application options for MCRs, such as MCR nanosystems and mechanochemical reactions [65].…”

Section: Methodsmentioning

confidence: 99%

Synergy Effects in the Chemical Synthesis and Extensions of Multicomponent Reactions (MCRs)—The Low Energy Way to Ultra-Short Syntheses of Tailor-Made Molecules

Eckert

2017

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Synergistic effects between reactions, reagents and catalysts can lead to minor heats of reaction and occur as an inherent result of multi-component reactions (MCRs) and their extensions. They enable syntheses to be performed at a low energy level and the number of synthesis steps to be drastically reduced in comparison with 'classical' two-component reactions. The very high potential for variability, diversity and complexity of MCRs additionally generates an extremely diverse range of products, thus bringing us closer to the aim of being able to produce tailor-made and extremely low-priced materials, drugs and libraries.Keywords: multicomponent reaction; MCR; post condensation modification PCM; post condensation cyclisation PCC; MFCR; multifunction catalysis; variability; diversity; complexity; efficiency of synthesis. PrologueThe high discrepancy between traditional feasibility mania and rational efficiency assessment in chemical synthesis became immediately apparent to the author while working on his thesis and during everyday laboratory life. On the one hand, classic peptide synthesis with an inefficient, extremely high number of synthesis steps and on the other hand, elegant multicomponent reactions that can make such efforts unnecessary. This double strategy in chemical synthesis has given the author cause to reflect (Picture 2) on how to close this gap using a consistent procedure. Picture 2. Problem in chemical syntheses relating to terms of producibility, ecology and economy.

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“…Despite some contributions on the application of carbohydrates or their derivatives in DOS have appeared in the literature recently, there are no examples of DOS strategies that combine the Petasis reaction with hexoses as building blocks. In fact, the Petasis reaction starting from carbohydrates has been used mainly in the total synthesis of natural products, including conduramine, pyrrolidine alkaloids, calystegine B4, and hyacinthacine C 5 . However, there is still room left for the exploitation of this multicomponent reaction with carbohydrates, especially for the construction of high quality chemical libraries following DOS principles.…”

Section: Introductionmentioning

confidence: 99%

A Glucose‐Derived α‐Hydroxy Aldehyde for the Petasis Reaction: Facile Access to Polyfunctional δ‐Amino Acids

et al. 2020

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The multicomponent Petasis borono‐Mannich reaction proceeds via an imine with the boronic acid acting as the nucleophile for the preparation of amines and their derivatives, including amino acids. In view of the expansion of the poorly‐exploited carbohydrate chemistry using this reaction, a new α‐hydroxy aldehyde moiety from the terminal diol of d‐glucose diacetonide was synthesized and applied to this multicomponent reaction, demonstrating the scope of this method and the applicability to the convenient preparation of a protected polyfunctional δ‐amino acid in only three synthetic steps from the Petasis reaction intermediate.

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The boronic acid Mannich reaction in alkaloid synthesis

Abstract: Our work on the application of the boronic acid Mannich reaction to the synthesis of pyrrolizidine alkaloids is described.

Cited by 9 publications

References 25 publications

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

Synergy Effects in the Chemical Synthesis and Extensions of Multicomponent Reactions (MCRs)—The Low Energy Way to Ultra-Short Syntheses of Tailor-Made Molecules

A Glucose‐Derived α‐Hydroxy Aldehyde for the Petasis Reaction: Facile Access to Polyfunctional δ‐Amino Acids

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The boronic acid Mannich reaction in alkaloid synthesis

Abstract: Our work on the application of the boronic acid Mannich reaction to the synthesis of pyrrolizidine alkaloids is described.

Cited by 9 publications

References 25 publications

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

Reactivity and Synthetic Applications of Multicomponent Petasis Reactions

Synergy Effects in the Chemical Synthesis and Extensions of Multicomponent Reactions (MCRs)&mdash;The Low Energy Way to Ultra-Short Syntheses of Tailor-Made Molecules

A Glucose‐Derived α‐Hydroxy Aldehyde for the Petasis Reaction: Facile Access to Polyfunctional δ‐Amino Acids

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Synergy Effects in the Chemical Synthesis and Extensions of Multicomponent Reactions (MCRs)—The Low Energy Way to Ultra-Short Syntheses of Tailor-Made Molecules