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Gram Scale Synthesis Of The C(18)-C(34) Fragment Of Amphidinolide C., Nicholas A Morra, Brian L Pagenkopf
Gram Scale Synthesis Of The C(18)-C(34) Fragment Of Amphidinolide C., Nicholas A Morra, Brian L Pagenkopf
Chemistry Publications
The synthesis of the C(18)-C(34) fragment of amphidinolide C has been achieved via two routes, culminating in both the shortest (11 steps) and highest yielding (26% overall yield) approaches to this segment. The highly convergent approach will facilitate the synthesis of analogues, including the C(18)-C(29) fragment of amphidinolide F. Synthetic highlights include the selective methylation of a diyne, and the highly efficient use of a second generation cobalt catalyst in the Mukaiyama oxidative cyclization to form the trans-THF ring.
Gram Scale Synthesis Of The C(18)-C(34) Fragment Of Amphidinolide C., Nicholas A Morra, Brian L Pagenkopf
Gram Scale Synthesis Of The C(18)-C(34) Fragment Of Amphidinolide C., Nicholas A Morra, Brian L Pagenkopf
Chemistry Publications
The synthesis of the C(18)-C(34) fragment of amphidinolide C has been achieved via two routes, culminating in both the shortest (11 steps) and highest yielding (26% overall yield) approaches to this segment. The highly convergent approach will facilitate the synthesis of analogues, including the C(18)-C(29) fragment of amphidinolide F. Synthetic highlights include the selective methylation of a diyne, and the highly efficient use of a second generation cobalt catalyst in the Mukaiyama oxidative cyclization to form the trans-THF ring.
Ytterbium Triflate Catalyzed Synthesis Of Alkoxy-Substituted Donor-Acceptor Cyclobutanes And Their Formal [4 + 2] Cycloaddition With Imines: Stereoselective Synthesis Of Piperidines., Mahmoud M Abd Rabo Moustafa, Brian L Pagenkopf
Ytterbium Triflate Catalyzed Synthesis Of Alkoxy-Substituted Donor-Acceptor Cyclobutanes And Their Formal [4 + 2] Cycloaddition With Imines: Stereoselective Synthesis Of Piperidines., Mahmoud M Abd Rabo Moustafa, Brian L Pagenkopf
Chemistry Publications
A new synthesis of 2-alkoxy-1,1-cyclobutane diesters and their first use in dipolar cycloadditions is reported. Both the formation of the donor-acceptor cyclobutanes and their subsequent annulation with in situ formed imines are catalyzed by Yb(OTf)(3). Cyclobutanes with carbon donor groups give piperidines with high trans stereoselectivity.
Formal [4 + 2] Cycloaddition Of Alkoxy-Substituted Donor-Acceptor Cyclobutanes And Aldehydes Catalyzed By Yb(Otf)3., Mahmoud M Abd Rabo Moustafa, Andrew C Stevens, Ben P Machin, Brian L Pagenkopf
Formal [4 + 2] Cycloaddition Of Alkoxy-Substituted Donor-Acceptor Cyclobutanes And Aldehydes Catalyzed By Yb(Otf)3., Mahmoud M Abd Rabo Moustafa, Andrew C Stevens, Ben P Machin, Brian L Pagenkopf
Chemistry Publications
The cycloaddition between 2-alkoxy-1,1-cyclobutane diesters and aromatic, heteroaromatic, or aliphatic aldehydes under Yb(OTf)(3) catalysis generates tetrahydropyrans in high yields with exclusive cis-stereochemistry.
Diels-Alder Chemistry Of Siloles And Their Transformation Into Cyclohex-2-Ene-1,4-Cis-Diols., Andrew C Stevens, Brian L Pagenkopf
Diels-Alder Chemistry Of Siloles And Their Transformation Into Cyclohex-2-Ene-1,4-Cis-Diols., Andrew C Stevens, Brian L Pagenkopf
Chemistry Publications
The synthesis of siloles with substitution patterns that are continuative toward natural product synthesis are described. Their reactivity in Diels-Alder chemistry was explored through thermal, Lewis acid, and high-pressure reactions. Furthermore, bicyclic adducts were oxidatively cleaved to reveal a highly functionalized cyclohexene core.
Increased Yields And Simplified Purification With A Second-Generation Cobalt Catalyst For The Oxidative Formation Of Trans-Thf Rings., Cory Palmer, Nicholas A Morra, Andrew C Stevens, Barbora Bajtos, Ben P Machin, Brian L Pagenkopf
Increased Yields And Simplified Purification With A Second-Generation Cobalt Catalyst For The Oxidative Formation Of Trans-Thf Rings., Cory Palmer, Nicholas A Morra, Andrew C Stevens, Barbora Bajtos, Ben P Machin, Brian L Pagenkopf
Chemistry Publications
The synthesis of a second-generation cobalt catalyst for the formation of trans-THF products via the Mukaiyama aerobic oxidative cyclization is reported. Two procedures have been developed with the new water-soluble catalyst that give superior yields and greatly simplify purification compared to the previous catalysts.
A General Asymmetric Aldol Reaction Of Silyl Ketene Acetals Derived From Simple Esters To Aryl Alpha-Ketoesters, Brian Pagenkopf, Julie Le Engers
A General Asymmetric Aldol Reaction Of Silyl Ketene Acetals Derived From Simple Esters To Aryl Alpha-Ketoesters, Brian Pagenkopf, Julie Le Engers
Chemistry Publications
No abstract provided.