Achmatowicz rearrangement - 50 years of application

• Autorzy: Grynkiewicz Grzegorz , Bielski Roman

Identyfikatory

DOI

10.15199/180.2020.4.2

Warianty tytułu

PL

Pół wieku zastosowań przegrupowania Achmatowicza

• Języki publikacji: EN

Abstrakty

EN

Chemical sciences proved instrumental in formulating theories and in providing materials which are crucial for development of contemporary technical civilization. Methods of chemical synthesis, necessary for supply of materials designed for specific technical needs have attained efficiency, which allows preparation of even most complicated molecules encountered in Nature. Academic stereo- and enantioselective total syntheses of natural products (such as: alkaloids, peptides, isoprenoids, lipids, carbohydrates and phenolics) are generally regarded as the top achievements of XX century organic chemistry. Along the line, this paper recalls ingenious project of total synthesis from simple furan derivatives, of pyranes and pyranosides, basic stuff of natural carbohydrates, suitably functionalized for a stepwise conversion into variety of sugar structures. The project designed in the Institute of Organic Chemistry, Polish Academy of Sciences in Warsaw, began its proof of principle experimental validation in 1970. Its success led to a widespread application of what is presently known as the Achmatowicz reaction/Achmatowicz rearrangement for syntheses of simple and complex, oxygen and nitrogen heterocyclic systems, including great variety of natural products.

PL

Nauki chemiczne odegrały kluczową rolę w kształtowaniu zarówno podstaw teoretycznych jak i zaplecza materialnego współczesnej cywilizacji przemysłowej. Metody syntezy chemicznej, niezbędne do wytwarzania materiałów technicznych o pożądanych właściwościach, osiągnęły sprawność pozwalającą na otrzymanie związków odpowiadających cząsteczkom organicznym pochodzenia biologicznego, o najwyższym stopniu złożoności. Syntezy totalne, stereo- i enancjoselektywne, związków naturalnych (alkaloidów, peptydów, izoprenoidów, lipidów, węglowodanów i związków fenolowych) uznano za najważniejsze osiągnięcia klasycznej chemii organicznej. Poniżej przedstawiamy genezę i rozwój projektu totalnej syntezy z prostych pochodnych furanu, wielofunkcyjnych piranów i piranoz - zasadniczej heterocyklicznej sześcioczłonowej struktury pierścieniowej naturalnych cukrów, glikozydów i ich oligomerycznych pochodnych, opracowanego w Instytucie Chemii Organicznej PAN w Warszawie, który w 1970-tym roku osiągnął zrealizowaną z powodzeniem fazę weryfikacji doświadczalnej. Osiągnięcie, które zyskało nazwę reakcji (przegrupowania) Achmatowicza, stanowi obecnie jedno z popularniejszych narzędzi stereokontrolowanej syntezy tlenowych i azotowych związków heterocyklicznych.

Słowa kluczowe

EN

furylcarbinols; pyrans; pyranoses; monosaccharides; total syntheses of natural and modified sugars; unsaturated sugars; Achmatowicz rearrangement

PL

furylokarbinole; pirany; piranozy; monosacharydy; totalne syntezy cukrów prostych; piranozy nienasycone; przegrupowanie Achmatowicza

• Wydawca: Wydawnictwo SIGMA-NOT
• Czasopismo: Polish Technical Review
• Rocznik: 2020
• Tom: No. 4
• Strony: 16--27
• Opis fizyczny: Bibliogr. 122 poz., rys.

Twórcy

autor

Grynkiewicz Grzegorz

• Professor Emeritus, Pharmaceutical Research Institute, Rydygiera 8, 01-793 Warszawa

autor

Bielski Roman

• Department of Pharmaceutical Sciences, Wilkes University, Wilkes-Barre PA 18766, USA

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Uwagi

Opracowanie rekordu ze środków MNiSW, umowa Nr 461252 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2021).