Asymmetric total synthesis of cryptoconcatone I

Literature Information

Publication Date 2019-03-12
DOI 10.1039/C9OB00399A
Impact Factor 3.876
Authors

Ranjan Kumar Acharyya, Pratik Pal, Shrestha Chatterjee, Samik Nanda


View Original

Abstract

Asymmetric total synthesis of the naturally occurring cryptoconcatone I, which possesses a γ-Z-butenolide framework, is described here for the first time. Asymmetric propargylation, E-selective cross metathesis, and regioselective reductive epoxide ring opening were employed to access the enantiopure terminal alkyne. Late stage bimetallic cascade cyclization of the alkyne with (Z)-3-bromoacrylic acid afforded the natural product in an efficient way.

Related Literature

Liberation of three dihydrogens from two ethene molecules as mediated by the tantalum nitride anion cluster Ta3N2− at room temperature

Ji-Chuang Hu, Lin-Lin Xu, Hai-Fang Li, David Yubero Valdivielso, André Fielicke, Sheng-Gui He, Jia-Bi Ma

2016-11-29 Paper

DOI: 10.1039/C6CP06896K

Jahn–Teller effect in LiMn2O4: influence on charge ordering, magnetoresistance and battery performance

K. Ragavendran, H. Xia, P. Mandal, A. K. Arof

2016-12-12 Paper

DOI: 10.1039/C6CP07289E

Screening out unfeasible hypothetical zeolite structures via the closest non-adjacent O⋯O pairs

Junran Lu, Lin Li, Hongxiao Cao, Yi Li, Jihong Yu

2016-12-06 Paper

DOI: 10.1039/C6CP06217B

Sensitized ZnO nanorod assemblies to detect heavy metal contaminated phytomedicines: spectroscopic and simulation studies

Damayanti Bagchi, Tuhin Kumar Maji, Samim Sardar, Chinmoy Bhattacharya, Debjani Karmakar, Samir Kumar Pal

2016-12-20 Paper

DOI: 10.1039/C6CP08016B

The discrete nature of inhomogeneity: the initial stages and local configurations of TiOPc during bilayer growth on Ag(111)

Laura Fernandez, Sebastian Thussing, Alexander Mänz, Jörg Sundermeyer, Gregor Witte, Peter Jakob

2016-12-22 Paper

DOI: 10.1039/C6CP07922A

Structural phase transitions of (Bi1−xSbx)2(Te1−ySey)3 compounds under high pressure and the influence of the atomic radius on the compression processes of tetradymites

Zhenhai Yu, Yong Wang, John Schneeloch, Chunyu Li, Ruidan Zhong, Zhiguo Liu, Genda Gu

2016-12-14 Paper

DOI: 10.1039/C6CP07324G

You might also like

Compound Q&A

Is 2-(2-chloroacetamido)-3-phenylpropanoic acid (CAS: 7765-11-9) safe?

2-(2-Chloroacetamido)-3-phenylpropanoic acid (CAS: 7765-11-9) is generally consi...

7765-11-92-(2-chloroacetamido...
Compound Q&A

Is 2-(Benzyloxy)-5-bromobenzoic acid (CAS: 62176-31-2) safe?

2-(Benzyloxy)-5-bromobenzoic acid can be handled safely if appropriate precautio...

62176-31-22-(Benzyloxy)-5-brom...
Compound Q&A

What is (4-Methyl-1,2,5-oxadiazol-3-yl)methanamine hydrochloride (CAS: 1159825-48-5)?

(4-Methyl-1,2,5-oxadiazol-3-yl)methanamine hydrochloride is a chemical compound ...

1159825-48-5(4-Methyl-1,2,5-oxad...
Compound Q&A

What is 2-(5-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS: 917985-54-7)?

2-(5-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS: 917985-54...

917985-54-72-(5-Hexylthiophen-2...
Compound Q&A

Are there alternatives to 4-(8-Methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-5-yl)benzenamine (CAS: 102771-26-6) in synthesis?

While 4-(8-Methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-5-yl)benzenamine (CAS:...

102771-26-64-(8-Methyl-9H-1,3-d...
Compound Q&A

What is the market or research trend for tert-butyl 3-hydroxy-4,5,7,8-tetrahydro-2H-pyrazolo[3,4-d]azepine-6-carboxylate (CAS: 851376-80-2)?

The market for tert-butyl 3-hydroxy-4,5,7,8-tetrahydro-2H-pyrazolo[3,4-d]azepine...

851376-80-2tert-butyl 3-hydroxy...
Compound Q&A

How should waste containing 3,5-Diamino-1H-pyrazole-4-carbonitrile (CAS: 6844-58-2) be handled?

Waste containing 3,5-Diamino-1H-pyrazole-4-carbonitrile (CAS: 6844-58-2) should ...

6844-58-23,5-Diamino-1H-pyraz...
Compound Q&A

How is (6-Fluoro-3-pyridinyl)boronic acid (CAS: 351019-18-6) typically synthesized?

(6-Fluoro-3-pyridinyl)boronic acid can be synthesized through the reaction of 6-...

351019-18-6(6-Fluoro-3-pyridiny...
Compound Q&A

What industries use Dibenzyl carbonimidoylbiscarbamate (CAS: 10065-79-9)?

Dibenzyl carbonimidoylbiscarbamate (CAS: 10065-79-9) finds applications in vario...

10065-79-9Dibenzyl carbonimido...
Compound Q&A

What is the market or research trend for (beta,beta,2,3,4,5,6-~2~H_7_)Phenylalanine (CAS: 74228-83-4)?

The market for (beta,beta,2,3,4,5,6-~2~H_7_)Phenylalanine (CAS: 74228-83-4) is g...

74228-83-4(beta,beta,2,3,4,5,6...

Source Journal

Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
Self-citation Rate: 10.3%
Articles per Year: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.