A site- and stereoselective intermolecular alkene-alkyne coupling process.
Explore the source record for details and available documents.
Alkenes↗
Biomedical subjects
Glenn C Micalizio
Publications and source records attributed to Glenn C Micalizio.
Studies on the syntheses of benzoquinone ansamycin antibiotics. Syntheses of the C5-C15 subunits of macbecin I, geldanamycin, and herbimycin A.
[reaction: see text] A general and convergent route to the C(5)-C(15) subunits of the benzoquinone ansamycin antibiotics macbecin I, geldanamycin, and herbimycin A is described. Each subunit is prepared by the stepwise coupling of differentially functionalized aldehydes with a pentenyl dianion equivalent derived from diastereoselective pentynylation and regioselective reductive coupling.
Anti-Bacterial Agents↗
Studies in macrolide antibiotic synthesis: the role of tethered alkoxides in titanium alkoxide-mediated regioselective reductive coupling reactions.
[reaction: see text] A convergent route to a C1-C15 fragment precursor for erythromycin-based macrolide antibiotics is presented. These studies define a role for tethered alkoxides in the control of site-selective carbon-carbon bond formation in titanium alkoxide-mediated coupling reactions of internal alkynes and chiral aldehydes.
Alcohols↗
An alkoxide-directed carbometalation of internal alkynes.
A mild and efficient alkoxide-directed carbometalation is described. Regioselective carbon-carbon bond formation occurs in all cases at the site distal to the tethered alkoxide. This reaction provides a convenient means to prepare differentially functionalized tetrasubstituted 1,3-dienes in a regio- and stereoselective manner.
Journal Article↗
Group 4 metals in polyketide synthesis: a convergent strategy for the synthesis of polypropionate-derived (E,E)-trisubstituted 1,3-dienes.
[reaction: see text] A convergent Group 4 metal-mediated coupling process is described for the synthesis of polypropionate-derived (E,E)-1,3-dienes. Both the stereochemistry of the internal alkyne and the presence/absence of a tethered alkoxide on this pi-component were found to play critical roles in dictating the regiochemical course of these reactions.
Alkenes↗
A pentenyl dianion-based strategy for convergent synthesis of ene-1,5-diols.
A convergent two-step process is described for the synthesis of ene-1,5-diols that provides for union of two carbonyl electrophiles via a formal pentenyl dianion equivalent.
Alcohols↗
Enantio- and diastereoselective synthesis of cyclic beta-hydroxy allylsilanes via sequential aldehyde gamma-silylallylboration and ring-closing metathesis reactions.
[reaction: see text] Highly enantioenriched cyclic allylsilanes are prepared via stereoselective gamma-silylallylboration reactions of beta- or gamma-unsaturated aldehydes followed by ring-closing metathesis.
Aldehydes↗
An alkynylboronic ester annulation: development of synthetic methods for application to diversity-oriented organic synthesis.
Explore the source record for details and available documents.
Boron Compounds↗
A boronic ester annulation strategy for diversity-oriented organic synthesis.
Explore the source record for details and available documents.
Boron Compounds↗