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Chemistry

Western University

Chemistry Publications

2011

Cyclization

Articles 1 - 2 of 2

Full-Text Articles in Physical Sciences and Mathematics

Gram Scale Synthesis Of The C(18)-C(34) Fragment Of Amphidinolide C., Nicholas A Morra, Brian L Pagenkopf Feb 2011

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 Jan 2011

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.