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Literature DB >> 24313360

Radical [3 + 2]-annulation of divinylcyclopropanes: rapid synthesis of complex meloscine analogs.

Hanmo Zhang¹, Kyu Ok Jeon, E Ben Hay, Steven J Geib, Dennis P Curran, Matthew G LaPorte.

Abstract

A radical [3 + 2]-divinylcyclopropane annulation cascade has been extended to encompass five D-ring variants of the meloscine/epimeloscine core structure. Representative ABCD tetracyclic intermediates were further elaborated with novel substituted E-rings through subsequent transformations of advanced intermediates that provided opportunities for late-stage variation of the B-ring (lactam) N-substituents which were also developed.

Entities: Chemical Disease Gene

Mesh：

Substances：

Year: 2013 PMID： 24313360 PMCID： PMC3910537 DOI： 10.1021/ol403078e

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

24 in total

Review 1. Natural products as sources of new drugs over the 30 years from 1981 to 2010.

Authors: David J Newman; Gordon M Cragg
Journal: J Nat Prod Date: 2012-02-08 Impact factor: 4.050

2. Transition metal chemistry of cyclopropenes and cyclopropanes.

Authors: Michael Rubin; Marina Rubina; Vladimir Gevorgyan
Journal: Chem Rev Date: 2007-07 Impact factor: 60.622

3. Quantifying structure and performance diversity for sets of small molecules comprising small-molecule screening collections.

Authors: Paul A Clemons; J Anthony Wilson; Vlado Dančík; Sandrine Muller; Hyman A Carrinski; Bridget K Wagner; Angela N Koehler; Stuart L Schreiber
Journal: Proc Natl Acad Sci U S A Date: 2011-04-11 Impact factor: 11.205

4. Allenyl azide cycloaddition chemistry: application to the total synthesis of (±)-meloscine.

Authors: Ken S Feldman; Joshua F Antoline
Journal: Org Lett Date: 2012-01-13 Impact factor: 6.005

5. Fe-catalyzed allylic C-C-bond activation: vinylcyclopropanes as versatile a1,a3,d5-synthons in traceless allylic substitutions and [3 + 2]-cycloadditions.

Authors: André P Dieskau; Michael S Holzwarth; Bernd Plietker
Journal: J Am Chem Soc Date: 2012-03-08 Impact factor: 15.419

6. Density functional theory study of the mechanisms and stereochemistry of the Rh(I)-catalyzed intramolecular [3+2] cycloadditions of 1-ene- and 1-yne-vinylcyclopropanes.

Authors: Lei Jiao; Mu Lin; Zhi-Xiang Yu
Journal: J Am Chem Soc Date: 2010-12-17 Impact factor: 15.419

Radical [3 + 2]-annulation of divinylcyclopropanes: rapid synthesis of complex meloscine analogs.

Review 1. Natural products as sources of new drugs over the 30 years from 1981 to 2010.

2. Transition metal chemistry of cyclopropenes and cyclopropanes.

3. Quantifying structure and performance diversity for sets of small molecules comprising small-molecule screening collections.

4. Allenyl azide cycloaddition chemistry: application to the total synthesis of (±)-meloscine.

5. Fe-catalyzed allylic C-C-bond activation: vinylcyclopropanes as versatile a1,a3,d5-synthons in traceless allylic substitutions and [3 + 2]-cycloadditions.

6. Density functional theory study of the mechanisms and stereochemistry of the Rh(I)-catalyzed intramolecular [3+2] cycloadditions of 1-ene- and 1-yne-vinylcyclopropanes.

7. Reaction of alpha-ene-vinylcyclopropanes: type II intramolecular [5+2] cycloaddition or [3+2] cycloaddition?

8. Palladium-catalyzed diastereo- and enantioselective formal [3 + 2]-cycloadditions of substituted vinylcyclopropanes.

Review 9. Function-oriented synthesis, step economy, and drug design.

10. Escape from flatland: increasing saturation as an approach to improving clinical success.

1. Synthesis of (±)-tetrapetalone A-Me aglycon.

2. Highly functionalized donor-acceptor cyclopropanes applied toward the synthesis of the Melodinus alkaloids.

3. Rearrangement reactions of 1,1-divinyl-2-phenylcyclopropanes.