Construction of the tetracyclic core of (±)-cycloclavine and 4-amino Uhle's ketone

Literature Information

Publication Date 2018-05-09
DOI 10.1039/C7OB03067C
Impact Factor 3.876
Authors

Jin-Quan Chen, Yang Mi, Zi-Fa Shi, Xiao-Ping Cao


View Original

Abstract

A rapid construction of the tetracyclic core (±)-2 of (±)-cycloclavine (1) was accomplished in seven steps and 24% overall yield from commercially available aldehyde 7. Key features include a domino Friedel–Crafts/nitro-Michael reaction to construct the C ring and an intramolecular ammonolysis of a diester to close the D ring. In addition, a versatile 4-amino Uhle's ketone (±)-3 was afforded rapidly in five steps and 43% overall yield.

Related Literature

New insights into the chemistry of ionic alkylorganic carbonates: a computational study

Khaleel I. Assaf, Abdussalam K. Qaroush, Ala'a F. Eftaiha

2017-05-17 Paper

DOI: 10.1039/C7CP02087B

Delineating the role of ripples on the thermal expansion of 2D honeycomb materials: graphene, 2D h-BN and monolayer (ML)-MoS2

P. Anees, M. C. Valsakumar, B. K. Panigrahi

2017-03-24 Paper

DOI: 10.1039/C6CP08635G

Molecular organization in the twist–bend nematic phase by resonant X-ray scattering at the Se K-edge and by SAXS, WAXS and GIXRD

W. D. Stevenson, Z. Ahmed, X. B. Zeng, C. Welch, G. H. Mehl

2017-05-03 Communication

DOI: 10.1039/C7CP01404J

Editorial of the PCCP themed issue on “Physical Chemistry for Life Sciences”

Christoph van Wüllen, Kirsten Schwing, Christoph Riehn, Markus Gerhards

2017-04-19 Editorial

DOI: 10.1039/C7CP90069D

Back cover

Cover

DOI: 10.1039/C7CP90141K

Contents list

Front/Back Matter

DOI: 10.1039/C7CP90121F

Ultrathin CoOx-modified hematite with low onset potential for solar water oxidation

Chun Du, Jun Wang, Xiao Liu, Jie Yang, Kun Cao, Yanwei Wen

2017-05-22 Paper

DOI: 10.1039/C7CP01588G

Reduction and oxidation of Au adatoms on the CeO2(111) surface – DFT+U versus hybrid functionals

Christopher Penschke, Joachim Paier

2017-04-24 Paper

DOI: 10.1039/C7CP01785E

Intracellular-molecular changes in plasma-irradiated budding yeast cells studied using multiplex coherent anti-Stokes Raman scattering microscopy

Ryo Furuta, Naoyuki Kurake, Kenji Ishikawa, Keigo Takeda, Hiroshi Hashizume, Hiroki Kondo, Takayuki Ohta, Masafumi Ito, Makoto Sekine, Masaru Hori

2017-04-27 Communication

DOI: 10.1039/C7CP00489C

You might also like

Compound Q&A

How should waste containing N-Methoxy-N-methyl-1,3-thiazole-5-carboxamide (CAS: 898825-89-3) be handled?

Waste containing N-Methoxy-N-methyl-1,3-thiazole-5-carboxamide (CAS: 898825-89-3...

898825-89-3N-Methoxy-N-methyl-1...
Compound Q&A

How should N-(4-Biphenylyl)dibenzo[b,d]furan-4-amine (CAS: 1318338-47-4) be stored?

N-(4-Biphenylyl)dibenzo[b,d]furan-4-amine should be stored in a tightly sealed c...

1318338-47-4N-(4-Biphenylyl)dibe...
Compound Q&A

What is the market or research trend for 3-Acetamido-5-amino-2,4,6-triiodobenzoic acid (CAS: 1713-07-1)?

The market for 3-Acetamido-5-amino-2,4,6-triiodobenzoic acid (CAS: 1713-07-1) is...

1713-07-13-Acetamido-5-amino-...
Compound Q&A

How should Benzyl 2-O-acetyl-3,4,6-tri-O-benzyl-beta-D-galactopyranoside (CAS: 61820-03-9) be stored?

Benzyl 2-O-acetyl-3,4,6-tri-O-benzyl-beta-D-galactopyranoside (CAS: 61820-03-9) ...

61820-03-9Benzyl 2-O-acetyl-3,...
Compound Q&A

What regulatory guidelines apply to 2-Ethylpiperazine dihydrochloride (CAS: 438050-52-3)?

2-Ethylpiperazine dihydrochloride (CAS: 438050-52-3) is regulated under the Glob...

438050-52-32-Ethylpiperazine di...
Compound Q&A

What regulatory guidelines apply to 1,1'-[1,3-Phenylenebis(methylene)]bis(3-methyl-1H-pyrrole-2,5-dione) (CAS: 119462-56-5)?

1,1'-[1,3-Phenylenebis(methylene)]bis(3-methyl-1H-pyrrole-2,5-dione) (CAS: 11946...

119462-56-51,1'-[1,3-Phenyleneb...
Compound Q&A

Are there alternatives to 5-Fluoro-2-(1-pyrrolidinyl)pyridine (CAS: 1287217-79-1) in synthesis?

Several alternatives can be used in the synthesis of 5-Fluoro-2-(1-pyrrolidinyl)...

1287217-79-15-Fluoro-2-(1-pyrrol...
Compound Q&A

What precautions should be taken when handling 6-Bromoimidazo[1,2-a]pyridin-8-amine (CAS: 676371-00-9)?

When handling 6-Bromoimidazo[1,2-a]pyridin-8-amine, it is important to wear appr...

676371-00-96-Bromoimidazo[1,2-a...
Compound Q&A

Are there alternatives to (2S,4R)-4-(4-Nitrobenzyl)pyrrolidine-2-carboxylic acid hydrochloride (CAS: 1049740-22-8) in synthesis?

Alternatives to (2S,4R)-4-(4-Nitrobenzyl)pyrrolidine-2-carboxylic acid hydrochlo...

1049740-22-8(2S,4R)-4-(4-Nitrobe...

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 Compounds

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.