Organotitanium reagents in organic synthesis a simple means to adjust reactivity and selectivity of carbanions

Reetz, Manfred T.

doi:10.1007/3-540-11766-0_1

Cited by 224 publications

(2 citation statements)

References 164 publications

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“…It was clear that a dramatic improvement would result from a direct axial methylation to install the C20 equatorial tertiary carbinol . Such a task is no small feat as the propensity for nucleophilic methylation reagents to add in an equatorial sense to substituted cyclohexanones is well-documented, , and there are few methods shown to reverse this selectivity. Shenvi had already noted the ineffectiveness of Yamamoto’s bulky aluminum reagents to deliver an axial methyl group to 102 , and this result was confirmed in our experiments.…”

Section: Resultsmentioning

confidence: 99%

Evolution of a Short and Stereocontrolled Synthesis of (+)-7,20-Diisocyanoadociane

et al. 2022

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A full account of the development of a concise and highly stereoselective synthesis of (+)-7,20-diisocyanoadociane (DICA)a structurally complex isocyanoditerpene with potent antiplasmodial activityis described. The strategy that evolved relies on the rapid construction of unsaturated tricyclic precursors designed to undergo stereocontrolled Birch reductions and a subsequent “bay ring” formation to generate the isocycloamphilectane core. This report is divided into three sections: (1) a description of the initial strategy and the results that focused our efforts on a single route to the DICA core, (2) a discussion of the precise choreography needed to enable a first-generation formal synthesis of (±)-DICA, and (3) the execution of a 13-step second-generation synthesis of (+)-DICA that builds on important lessons learned from the first-generation effort.

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Section: Resultsmentioning

confidence: 99%

Evolution of a Short and Stereocontrolled Synthesis of (+)-7,20-Diisocyanoadociane

et al. 2022

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“…13C NMR, 77 Alkanes, in super acid, 59 Alkenes, addition and polymerization, 57 amination, 131 bridgehead, 189 epoxidation with 02, 97 photochemistry, 165 Alienes, halo, 109 substituent effects, 177 vinyl, 14 Amines, from alkenes, 131 Amino groups, protection, 110 Anisotropic molecular solids, 93 Antibiotics, 194 macrolide, 6 mechanism of action, 1 Aromatic substitution by SRN1, 200 Asymmetric reductions, 151 Asymmetric hydroformylation, 142 Asymmetric hydrogenation, 99 Aza crown compounds, aliphatic, 116 Azaphenalenes, synthesis, 73 Azides, phosphorus acid, 111 Aziridines, 159 Azirines, 160 Azulenes, polycyclic, 115 pseudo, 34 Biosynthesis, macrolide antibiotics, 6 sulfur compounds, 133 Calixarenes, 19 Camptothecin, 155 Carbanions, photochemistry, 164 reactivity, 144 Carbocations, rearrangements, 43 di-, 56 vinyl, 191 Carbohydrates, cyclodextrins, 134 functionalization, 76 isocyanates, 81 Carbonyl groups, transposition, 66,129 IV-Chloroalkenylamines, homolytic cyclization, 55 Conformation and reactivity, 62 Conformation, conjugated systems, 108 nucleic acids, 90 Crown compounds, 106 Crystallographic data, 18 Cyclizations, intramolecular, 182 Nazarov, 122 Cyclodextrins, 134 Cyclopentadienyl metal compounds, 36 Dehalogenation, polyhalo ketones, 84 Dehydropeptides, 171 Deprotection, in pe...…”

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confidence: 99%