Journal of the American Chemical Society, volume 141, issue 1, pages 154-158

Concise Syntheses of Δ¹²-Prostaglandin J Natural Products via Stereoretentive Metathesis

Jiaming Li ¹

Tonia S. Ahmed ¹

Chen Xu ^{1, 2}

Brian M. Stoltz ¹

Robert K. Grubbs ¹

The Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States |

Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong 518000, China |

Publication type: Journal Article

Publication date: 2018-12-12

American Chemical Society (ACS)

Journal: Journal of the American Chemical Society

scimago Q1

SJR: 5.489

CiteScore: 24.4

Impact factor: 14.4

ISSN: 00027863, 15205126

DOI: 10.1021/jacs.8b12816

Copy DOI

PubMed ID: 30537831

General Chemistry

Catalysis

Biochemistry

Colloid and Surface Chemistry

Abstract

Δ12-Prostaglandin J family is recently discovered and has potent anticancer activity. Concise syntheses of four Δ12-prostaglandin J natural products (7-8 steps in the longest linear sequences) are reported, enabled by convergent stereoretentive cross-metathesis. Exceptional control of alkene geometry was achieved through stereoretention.

Found

	1 2 3 4
Organic Letters	Organic Letters, 4, 10% Organic Letters 4 publications, 10%
Journal of Organic Chemistry	Journal of Organic Chemistry, 3, 7.5% Journal of Organic Chemistry 3 publications, 7.5%
Mendeleev Communications	Mendeleev Communications, 2, 5% Mendeleev Communications 2 publications, 5%
Angewandte Chemie	Angewandte Chemie, 2, 5% Angewandte Chemie 2 publications, 5%
Angewandte Chemie - International Edition	Angewandte Chemie - International Edition, 2, 5% Angewandte Chemie - International Edition 2 publications, 5%
Chemical Science	Chemical Science, 2, 5% Chemical Science 2 publications, 5%
Russian Journal of Organic Chemistry	Russian Journal of Organic Chemistry, 1, 2.5% Russian Journal of Organic Chemistry 1 publication, 2.5%
New Journal of Chemistry	New Journal of Chemistry, 1, 2.5% New Journal of Chemistry 1 publication, 2.5%
International Journal of Molecular Sciences	International Journal of Molecular Sciences, 1, 2.5% International Journal of Molecular Sciences 1 publication, 2.5%
Nature Chemistry	Nature Chemistry, 1, 2.5% Nature Chemistry 1 publication, 2.5%
Russian Chemical Bulletin	Russian Chemical Bulletin, 1, 2.5% Russian Chemical Bulletin 1 publication, 2.5%
Tetrahedron	Tetrahedron, 1, 2.5% Tetrahedron 1 publication, 2.5%
Advanced Science	Advanced Science, 1, 2.5% Advanced Science 1 publication, 2.5%
Chemistry - A European Journal	Chemistry - A European Journal, 1, 2.5% Chemistry - A European Journal 1 publication, 2.5%
ChemistrySelect	ChemistrySelect, 1, 2.5% ChemistrySelect 1 publication, 2.5%
European Journal of Organic Chemistry	European Journal of Organic Chemistry, 1, 2.5% European Journal of Organic Chemistry 1 publication, 2.5%
Asian Journal of Organic Chemistry	Asian Journal of Organic Chemistry, 1, 2.5% Asian Journal of Organic Chemistry 1 publication, 2.5%
Journal of the American Chemical Society	Journal of the American Chemical Society, 1, 2.5% Journal of the American Chemical Society 1 publication, 2.5%
Green Chemistry	Green Chemistry, 1, 2.5% Green Chemistry 1 publication, 2.5%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 1, 2.5% Organic and Biomolecular Chemistry 1 publication, 2.5%
Synlett	Synlett, 1, 2.5% Synlett 1 publication, 2.5%
Catalysts	Catalysts, 1, 2.5% Catalysts 1 publication, 2.5%
Nature Communications	Nature Communications, 1, 2.5% Nature Communications 1 publication, 2.5%
Bulletin of the Chemical Society of Japan	Bulletin of the Chemical Society of Japan, 1, 2.5% Bulletin of the Chemical Society of Japan 1 publication, 2.5%
Tetrahedron Letters	Tetrahedron Letters, 1, 2.5% Tetrahedron Letters 1 publication, 2.5%
ACS Catalysis	ACS Catalysis, 1, 2.5% ACS Catalysis 1 publication, 2.5%
ChemMedChem	ChemMedChem, 1, 2.5% ChemMedChem 1 publication, 2.5%
JACS Au	JACS Au, 1, 2.5% JACS Au 1 publication, 2.5%
	1 2 3 4

	2 4 6 8 10 12
Wiley	Wiley, 11, 27.5% Wiley 11 publications, 27.5%
American Chemical Society (ACS)	American Chemical Society (ACS), 10, 25% American Chemical Society (ACS) 10 publications, 25%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 5, 12.5% Royal Society of Chemistry (RSC) 5 publications, 12.5%
Elsevier	Elsevier, 4, 10% Elsevier 4 publications, 10%
Springer Nature	Springer Nature, 3, 7.5% Springer Nature 3 publications, 7.5%
MDPI	MDPI, 2, 5% MDPI 2 publications, 5%
OOO Zhurnal "Mendeleevskie Soobshcheniya"	OOO Zhurnal "Mendeleevskie Soobshcheniya", 2, 5% OOO Zhurnal "Mendeleevskie Soobshcheniya" 2 publications, 5%
Pleiades Publishing	Pleiades Publishing, 1, 2.5% Pleiades Publishing 1 publication, 2.5%
Georg Thieme Verlag KG	Georg Thieme Verlag KG, 1, 2.5% Georg Thieme Verlag KG 1 publication, 2.5%
Oxford University Press	Oxford University Press, 1, 2.5% Oxford University Press 1 publication, 2.5%
	2 4 6 8 10 12

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.

Metrics

Cite this

GOST | RIS | BibTex | MLA

Found error?

Publisher

American Chemical Society (ACS)

Journal

Journal of the American Chemical Society

scimago Q1

SJR

5.489

CiteScore

24.4

Impact factor

14.4

ISSN

00027863 (Print)

15205126 (Electronic)

Concise Syntheses of Δ¹²-Prostaglandin J Natural Products via Stereoretentive Metathesis

Top-30

Journals

Publishers

Are you a researcher?

Concise Syntheses of Δ12-Prostaglandin J Natural Products via Stereoretentive Metathesis

Top-30

Journals

Publishers

Are you a researcher?

Concise Syntheses of Δ¹²-Prostaglandin J Natural Products via Stereoretentive Metathesis