Total synthesis of selected bioactive alkaloids, their structure–function relationships and molecular target interactions: A comparative synthetic analysis of tryptophan originated chiral pool approaches vs other synthons

Results in Chemistry, Journal Year: 2021, Volume and Issue: 3, P. 100215 - 100215

Published: Jan. 1, 2021

The use of tryptophan as an inexpensive and versatile chiral pool for alkaloid synthesis continues to influence modern synthetic chemistry. In this review, we summarized comparative strategies based alkaloids the construction architecturally complex bioactive natural compounds using tryptophan-derived synthons versus non-tryptophan routes on basis atom economy, overall chemical yield, stereoselectivity sustainability. We also briefly discussed Structure-activity relationship selected tryptophan-based & their modified analogous elevate effects in a broad spectrum pharmacological effects. Tryptophan has inherent chirality which makes it great advantage cheap Chiron having functionalizable groups (–CO2H, –NH2 indole) ensures at least one fixed center governs installation another stereogenic metal organocatalyzed asymmetric synthesis. On contrary, route utilizes external source generate molecule. approach, organometallic catalysts are used numerous transformations. With green chemistry approach being need hour industry research laboratories, economic sustainable total Tryptophan-derived will be guiding path forward.

Language: Английский

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Collective Syntheses of Corynanthe Alkaloids Based on a Chirality-Tunable Structure Unit

Organic Letters, Journal Year: 2024, Volume and Issue: 26(41), P. 8803 - 8809

Published: Oct. 8, 2024

A novel strategy based on a common intermediate bearing chirality-tunable structure unit for the collective syntheses of corynantheine-type and heteroyohimbine-type alkaloids has been developed. Key transformations synthetic are sequential nucleophilic C–N bond formation/Mannich-type cyclization to construct highly functional C/D rings, stereocontrolled introduction C15 C20 chiral centers unit, an amine-directed addition Me3Al C18 methyl group.

Language: Английский

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Enantioselective α-Functionalization of 1,3-Dithianes by Iridium-Catalyzed Allylic Substitution

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(19), P. 12456 - 12467

Published: Sept. 10, 2020

An iridium-catalyzed asymmetric allylic substitution reaction with 2-alkoxy carbonyl-1,3-dithianes has been achieved high regio- and enantioselectivities. The transformation provides a new method for the enantioselective α-functionalization of dithianes. corresponding dithiane-containing products are easily converted into many other derivatives yields

Language: Английский

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Catalytic Asymmetric Alkynylation of 3,4‐Dihydro‐β‐carbolinium Ions Enables Collective Total Syntheses of Indole Alkaloids

Angewandte Chemie, Journal Year: 2021, Volume and Issue: 133(47), P. 25339 - 25346

Published: Sept. 28, 2021

Abstract Chiral tetrahydro‐β‐carboline (THβC) is not only a prevailing structural feature of many natural alkaloids but also versatile synthetic precursor for vast array monoterpenoid indole alkaloids. Asymmetric synthesis C1‐alkynyl THβCs remains rarely explored and challenging. Herein, we describe the development two complementary approaches catalytic asymmetric alkynylation 3,4‐dihydro‐β‐carbolinium ions with up to 96 % yield 99 ee . The utility chiral was demonstrated by collective total syntheses seven alkaloids: harmicine, eburnamonine, desethyleburnamonine, larutensine, geissoschizol, geissochizine, akuammicine.

Language: Английский

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Übergangsmetallkatalysierte Kupplungsreaktionen

Springer eBooks, Journal Year: 2023, Volume and Issue: unknown, P. 615 - 751

Published: Jan. 1, 2023

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