First total synthesis of aspergillolide

被引：6

作者：

Subba, Srijana ^{[1
]}

Saha, Sumit ^{[1
]}

Mandal, Susanta ^{[2
]}

Ghosh, Amlan Jyoti ^{[3
]}

Saha, Tilak ^{[3
]}

机构：

[1] Natl Inst Technol Sikkim, Dept Chem, Ravangla 737139, South Sikkim, India

[2] Sikkim Univ, Dept Chem, Gangtok 737102, Sikkim, India

[3] Univ North Bengal, Dept Zool, Lab Immunol & Microbiol, Siliguri 734013, West Bengal, India

来源：

TETRAHEDRON LETTERS | 2022年 / 106卷

关键词：

Total synthesis; Macrolide; RCM; Epoxide; STEREOSELECTIVE TOTAL-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; MACROLIDES; ANTIBIOTICS;

D O I：

10.1016/j.tetlet.2022.154081

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of aspergillolide has been accomplished starting from commercially available D- glutamic acid, (S)-glycidol and (R)-3-butyn-2-ol as chiral resources. The key steps of presented convergent synthetic approach for the total synthesis of aspergillolide are epoxide ring opening reaction and ring closing metathesis (RCM). A preliminary antimicrobial assay of the synthesized compound has also been studied. (C) 2022 Elsevier Ltd. All rights reserved.

引用

页数：5

共 36 条

[1] Determination of minimum inhibitory concentrations [J].

Andrews, JM .

JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 2001, 48 :5-16

[2]

[Anonymous], 2012, Performance Standards for Antimicrobial Susceptibility Testing

[3]

Twenty-Second Informational Supplment

[4] 16-membered macrolide antibiotics: a review [J].

Arsic, Biljana ;

Barber, Jill ;

Cikos, Ana ;

Mladenovic, Milan ;

Stankovic, Nevena ;

Novak, Predrag .

INTERNATIONAL JOURNAL OF ANTIMICROBIAL AGENTS, 2018, 51 (03) :283-298

[5] Diastereo- and enantioselective synthesis of 1,3,5,7-tetraol structural units using a Prins cyclisation-reductive cleavage sequence [J].

Brun, Elodie ;

Bellosta, Veronique ;

Cossy, Janine .

CHEMICAL COMMUNICATIONS, 2014, 50 (51) :6718-6721

[6] Stereoselective synthesis of dendrodolide-L [J].

Bujaranipalli, Sheshurao ;

Das, Saibal .

TETRAHEDRON-ASYMMETRY, 2016, 27 (06) :254-260

[7] Culturable Microorganisms Associated with Sea Cucumbers and Microbial Natural Products [J].

Chen, Lei ;

Wang, Xiao-Yu ;

Liu, Run-Ze ;

Wang, Guang-Yu .

MARINE DRUGS, 2021, 19 (08)

[8] Asymmetric Total Synthesis of Bioactive Natural Lipid Mycalol [J].

Das, Subhendu ;

Kuilya, Tapan Kumar ;

Goswami, Rajib Kumar .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (12) :6467-6489

[9] The divergent asymmetric synthesis of kalafungin, 5-epi-frenolicin B and related pyranonaphthoquinone antibiotics [J].

Donner, Christopher D. .

TETRAHEDRON, 2013, 69 (01) :377-386

[10] Total Synthesis of Berkeleylactone A [J].

Ferko, Branislav ;

Zeman, Marian ;

Formica, Michele ;

Vesely, Sebastian ;

Dohanosova, Jana ;

Moncol, Jan ;

Olejnikova, Petra ;

Berkes, Dusan ;

Jakubec, Pavol ;

Dixon, Darren J. ;

Caletkova, O'ga .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (11) :7159-7165

← 1 2 3 4 →