Gram scale synthesis of the C(18)-C(34) fragment of amphidinolide C.
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.
Department of Chemistry, The University of Western Ontario, London, Ontario N6A 5B7, Canada.
Nicholas A
NA
Morra
Brian L
BL
Pagenkopf
D002384:Catalysis; D003035:Cobalt / Q000737:chemistry*; D003500:Cyclization; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D000097442:Amphidinolides
D003035:Cobalt; D018942:Macrolides; C072156:amphidinolide F; D000097442:Amphidinolides