4.8 Article

Total Synthesis of (+)-Mutilin: A Transannular [2+2] Cycloaddition/Fragmentation Approach

Related references

Note: Only part of the references are listed.
Article Chemistry, Multidisciplinary

Synthesis of Pleuromutilin

Nicholas J. Foy et al.

Summary: This paper describes the synthesis of a potent inhibitor of bacterial protein synthesis, pleuromutilin. The assembly of the critical cyclooctane fragment is achieved through an oxidative ring-expansion, and the complete stereochemical relay in the synthetic sequence is enabled by the careful choice of tactics. The necessary connectivity pattern of the perhydroindanone motif is rapidly established through a sequence of cycloaddition and radical cyclization events. By applying this strategy, the target natural product can be prepared in 16 steps from commercially available materials.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Chemistry, Multidisciplinary

Two-Phase Synthesis of Taxol

Yuzuru Kanda et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Multidisciplinary Sciences

Synthetic group A streptogramin antibiotics that overcome Vat resistance

Qi Li et al.

NATURE (2020)

Review Biochemistry & Molecular Biology

Antibacterial properties and clinical potential of pleuromutilins

Olivia Goethe et al.

NATURAL PRODUCT REPORTS (2019)

Article Chemistry, Multidisciplinary

Scalable Access to Arylomycins via C-H Functionalization Logic

David S. Peters et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Multidisciplinary

Total Synthesis of (+)-Pleuromutilin

Elliot P. Farney et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Multidisciplinary Sciences

Optimized arylomycins are a new class of Gram-negative antibiotics

Peter A. Smith et al.

NATURE (2018)

Article Chemistry, Multidisciplinary

Development of a Modular Synthetic Route to (+)-Pleuromutilin, (+)-12-epi-Mutilins, and Related Structures

Mingshuo Zeng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Multidisciplinary

Total Synthesis of Longeracinphyllin A

Jian Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Multidisciplinary Sciences

A modular and enantioselective synthesis of the pleuromutilin antibiotics

Stephen K. Murphy et al.

SCIENCE (2017)

Review Chemistry, Multidisciplinary

Total Syntheses of Vancomycin-Related Glycopeptide Antibiotics and Key Analogues

Akinori Okano et al.

CHEMICAL REVIEWS (2017)

Review Chemistry, Multidisciplinary

Targeting Antibiotic Resistance

Mathieu F. Chellat et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Review Chemistry, Multidisciplinary

Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis

Markus D. Karkas et al.

CHEMICAL REVIEWS (2016)

Review Multidisciplinary Sciences

Antibacterial drug discovery in the resistance era

Eric D. Brown et al.

NATURE (2016)

Article Multidisciplinary Sciences

A platform for the discovery of new macrolide antibiotics

Ian B. Seiple et al.

NATURE (2016)

Article Chemistry, Organic

Synthesis and synthetic chemistry of pleuromutilin

Neal J. Fazakerley et al.

TETRAHEDRON (2014)

Article Chemistry, Multidisciplinary

Synthesis of ent-Kaurane and Beyerane Diterpenoids by Controlled Fragmentations of Overbred Intermediates

Emily C. Cherney et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Article Chemistry, Multidisciplinary

Total Synthesis of (+)-Pleuromutilin

Neal J. Fazakerley et al.

CHEMISTRY-A EUROPEAN JOURNAL (2013)

Article Chemistry, Organic

The Claisen rearrangement in the syntheses of bioactive natural products

K. C. Majumdar et al.

TETRAHEDRON (2013)

Article Chemistry, Multidisciplinary

Total Synthesis of Oxidized Welwitindolinones and (-)-N-Methylwelwitindolinone C Isonitrile

Kyle W. Quasdorf et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Article Chemistry, Multidisciplinary

A concise synthesis of the molecular framework of pleuromutilin

Junjia Liu et al.

CHEMICAL COMMUNICATIONS (2011)

Article Chemistry, Multidisciplinary

Expanding the pleuromutilin class of antibiotics by de novo chemical synthesis

Stephen D. Lotesta et al.

CHEMICAL SCIENCE (2011)

Article Chemistry, Multidisciplinary

Ethynyl-1,2-benziodoxol-3(1H)-one (EBX): An Exceptional Reagent for the Ethynylation of Keto, Cyano, and Nitro Esters

Davinia Fernandez Gonzalez et al.

CHEMISTRY-A EUROPEAN JOURNAL (2010)

Article Chemistry, Multidisciplinary

A Dialdehyde Cyclization Cascade: An Approach to Pleuromutilin

Matthew D. Helm et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

Review Chemistry, Multidisciplinary

Antibacterial natural products in medicinal chemistry - Exodus or revival?

Franz von Nussbaum et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2006)

Article Multidisciplinary Sciences

Total synthesis of norzoanthamine

M Miyashita et al.

SCIENCE (2004)

Article Chemistry, Multidisciplinary

Aziridinomitosenes by anionic cyclization: Deuterium as a removable blocking group

E Vedejs et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2002)

Article Chemistry, Multidisciplinary

Ground- and excited-state surfaces for the [2+2]-photocycloaddition of α,β-enones to alkenes

S Wilsey et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2000)