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Journal articleBarrett AGM, Braddock DC, James RA, et al., 1997,
Nucleophilic substitution of (alkoxymethylene)dimethylammonium chloride with potassium phthalimide; A convenient procedure for the synthesis of imides with inversion of configuration
, Chemical Communications, Pages: 433-434, ISSN: 1359-7345 -
Journal articleAngell RM, Barrett AGM, Braddock DC, et al., 1997,
Enantioselective synthesis of homoallylic alcohols using (E)-but-2- enyl-trichlorosilane and chiral diamines
, Chemical Communications, Pages: 919-920, ISSN: 1359-7345 -
Journal articleBarrett AGM, Baugh SPD, Braddock DC, et al., 1997,
Enyne metathesis for the facile synthesis of highly functionalised novel bicyclic beta-lactams
, Chemical Communications, Pages: 1375-1376, ISSN: 1359-7345 -
Journal articleBarrett AGM, Braddock DC, 1997,
Scandium(III) or lanthanide(III) triflates as recyclable catalysts for the direct acetylation of alcohols with acetic acid
, Chemical Communications, Pages: 351-352, ISSN: 1359-7345 -
Journal articleBraddock DC, Tucker SC, Brown JM, 1997,
Reversible aromatic bromination induced by buttressing: 1-bromo and 8-bromo-3,6-di-tert-butyl-2-methoxynaphthalene
, Bulletin de la Societe Chimiques de France, Vol: 134, Pages: 399-410, ISSN: 0037-8968 -
Journal articleBarrett AGM, Baugh SPD, Braddock DC, et al., 1997,
Enyne metathesis for the facile synthesis of highly functionalised novel bicyclic beta-lactams
, Chemical Communications, Pages: 1375-1376, ISSN: 1359-7345 -
Journal articleWaller FJ, Barrett AGM, Braddock DC, et al., 1997,
Lanthanide(III) triflates as recyclable catalysts for atom economic aromatic nitration
, Chemical Communications, Pages: 613-614, ISSN: 1359-7345 -
Journal articleBraddock DC, Brown JM, Guiry PJ, 1993,
Stereochemistry of the catalysed diels-alder reaction between cyclopentadiene and dimethyl monothionofumarate
, Chemical Communications, Vol: 1993, Pages: 1244-1246, ISSN: 1359-7345 -
Journal articleBahou K, Braddock DC, Meyer AG, et al.,
A Relay Strategy Actuates Pre-Existing Trisubstituted Olefins in Monoterpenoids to Form New Trisubstituted Olefins by Cross Metathesis
<jats:p><b><u>Abstract:</u></b> A retrosynthetic disconnection-reconnection analysis of epoxypolyenes – substrates that can undergo cyclization to podocarpane-type tricycles – reveals relay-actuated Δ<sup>6,7</sup>-functionalized monoterpenoid alcohols for ruthenium benzylidene catalyzed olefin cross metathesis with homoprenyl benzenes. Successful implementation of this approach provided several epoxypolyenes as expected (<i>E</i>:<i>Z</i>, ca. 2-3:1). The method is further generalized for the cross metathesis of pre-existing trisubstituted olefins in other relay-actuated Δ<sup>6,7</sup>-functionalized monoterpenoid alcohols with various other trisubstituted alkenes to form new trisubstituted olefins. Epoxypolyene cyclization of an enantiomerically pure, but geometrically impure, epoxypolyene substrate provides an enantiomerically pure, trans-fused, podocarpane-type tricycle (from the <i>E</i>-geometrical isomer).<br></jats:p>
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Journal articleBahou K, Braddock DC, Meyer AG, et al.,
A Relay Strategy Actuates Pre-Existing Trisubstituted Olefins in Monoterpenoids to Form New Trisubstituted Olefins by Cross Metathesis
<jats:p><jats:bold><jats:underline>Abstract:</jats:underline></jats:bold> A retrosynthetic disconnection-reconnection analysis of epoxypolyenes – substrates that can undergo cyclization to podocarpane-type tricycles – reveals relay-actuated Δ<jats:sup>6,7</jats:sup>-functionalized monoterpenoid alcohols for ruthenium benzylidene catalyzed olefin cross metathesis with homoprenyl benzenes. Successful implementation of this approach provided several epoxypolyenes as expected (<jats:italic>E</jats:italic>:<jats:italic>Z</jats:italic>, ca. 2-3:1). The method is further generalized for the cross metathesis of pre-existing trisubstituted olefins in other relay-actuated Δ<jats:sup>6,7</jats:sup>-functionalized monoterpenoid alcohols with various other trisubstituted alkenes to form new trisubstituted olefins. Epoxypolyene cyclization of an enantiomerically pure, but geometrically impure, epoxypolyene substrate provides an enantiomerically pure, trans-fused, podocarpane-type tricycle (from the <jats:italic>E</jats:italic>-geometrical isomer).</jats:p><jats:p />
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Journal articleBahou K, Braddock DC, Meyer AG, et al.,
Relay Cross Metathesis for the Iterative Ascent of the Terpenoids
<jats:p>We report the design and implementation of a relay crossmetathesis (ReXM) reaction for the ascent of the terpenoids in an iterative protocol. The method features the reaction of naturally occurring terpenoid building blocks – with preexisting trisubstituted olefins – which combine to construct a new trisubstituted olefin resulting in a five-carbon unit homologation. Subsequent functional group manipulation allows for the method to be repeated in aniterative fashion. The method is used for the synthesis of a diterpenebenzoate macrolide of biogenetic relevance to the bromophycolide family of natural products.</jats:p>
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Journal articleBahou K, Braddock DC, Meyer AG, et al.,
Relay Cross Metathesis for the Ascent of the Terpenoids
<jats:p>We report the design and implementation of a relay cross metathesis (ReXM) reaction for the ascent of the terpenoids in an iterative protocol using naturally occurring terpenoid building blocks. The method is used for the synthesis of a diterpene-benzoate macrolide of biogenetic relevance to the bromophycolide family of natural products.</jats:p>
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