The Journal of Organic Chemistry 2017-05-11

Total Synthesis of γ-Indomycinone and Kidamycinone by Means of Two Regioselective Diels–Alder Reactions

Thibaud Mabit, Aymeric Siard, Mathilde Pantin, Doumadé Zon, Laura Foulgoc, Drissa Sissouma, André Guingant, Monique Mathé-Allainmat, Jacques Lebreton, François Carreaux, Gilles Dujardin, Sylvain Collet

Index: 10.1021/acs.joc.7b00544

Full Text: HTML

Abstract

An efficient access for the synthesis of pluramycinones is described. Total syntheses of racemic γ-indomycinone and kidamycinone were achieved by means of two Diels–Alder reactions. A first Diels–Alder condensation followed by a Stille cross-coupling is used for the elaboration of the desired substituted dienes which will be involved in the second pericyclic reaction with juglone to construct the tetracyclic core of pluramycinones.

Latest Articles:

Synthesis and Unique Optical Properties of Selenophenyl BODIPYs and Their Linear Oligomers

2018-04-19

[10.1021/acs.joc.8b00782]

Synthesis of 3,5-Disubstituted BODIPYs Bearing N-Containing Five-Membered Heteroaryl Groups via Nucleophilic C–N Bond Formation

2018-04-17

[10.1021/acs.joc.8b00087]

Steric Hindrance Underestimated: It is a Long, Long Way to Tri-tert-alkylamines

2018-04-17

[10.1021/acs.joc.8b00496]

Stereoselective Sequential [4+2]/[2+2] Cycloadditions Involving 2-Alkenylindolenines: An Approach to Densely Functionalized Benzo[b]indolizidines

2018-04-16

[10.1021/acs.joc.8b00346]

Pd-Induced Double C–H Bond Activation in Annulative Syntheses of Bipyrrole Boomerangs: Mechanistic Insights from NMR Spectroscopy and Computation

2018-04-16

[10.1021/acs.joc.8b00630]

More Articles...