J 2021

Stereocontrolled Synthesis of Pseurotin A(2)

JACHAK, Gorakhnath Rajaram, Prabhakara Rao THARRA, Petr SEVELDA and Jakub ŠVENDA

Basic information

Original name

Stereocontrolled Synthesis of Pseurotin A(2)

Authors

JACHAK, Gorakhnath Rajaram (356 India, belonging to the institution), Prabhakara Rao THARRA (356 India, belonging to the institution), Petr SEVELDA (203 Czech Republic, belonging to the institution) and Jakub ŠVENDA (203 Czech Republic, guarantor, belonging to the institution)

Edition

Journal of Organic Chemistry, Washington, D.C. American Chemical Society, 2021, 0022-3263

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

Impact factor

Impact factor: 4.198

RIV identification code

RIV/00216224:14310/21:00122547

Organization unit

Faculty of Science

UT WoS

000693628600047

Keywords in English

Mixtures; Organic compounds; Anions; Solutions; Ethyl groups

Tags

Tags

International impact, Reviewed
Změněno: 22/1/2024 11:08, Mgr. Pavla Foltynová, Ph.D.

Abstract

V originále

We report synthesis of two diastereomeric structures previously proposed for the complex secondary metabolite pseurotin A(2). Both structures were accessed from the same building blocks taking advantage of a stereodivergent nickel(II)-iamine-catalyzed 1,4-addition of a chiral 2-alkoxycarbonyl-3(2H)-furanone. Late-stage Csp-Csp(3) cross-coupling of a highly functionalized bromoalkyne featured in the pseurotin A(2) side-chain assembly. The work supports the 2016 stereochemical revision of pseurotin A(2) and represents the first chemical synthesis of this natural product.

Links

EF16_025/0007381, research and development project
Name: Preklinická progrese nových organických sloučenin s cílenou biologickou aktivitou
EF16_027/0008360, research and development project
Name: Postdoc@MUNI
LM2015063, research and development project
Name: Národní infrastruktura chemické biologie (Acronym: CZ-­OPENSCREEN)
Investor: Ministry of Education, Youth and Sports of the CR