Open AccessGram Scale Synthesis of the C(18)−C(34) Fragment of Amphidinolide C
Author(s) -
Nicholas A. Morra,
Brian L. Pagenkopf
Publication year - 2011
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/ol1030074
Subject(s) - chemistry , yield (engineering) , stereochemistry , total synthesis , fragment (logic) , ring (chemistry) , methylation , combinatorial chemistry , organic chemistry , dna , biochemistry , materials science , computer science , metallurgy , programming language
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.
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