Abstract:A concise and efficient synthesis of the proposed structure of aaptoline A, a 7,8-dihydroxyquinoline derived from a marine sponge, was accomplished in seven steps with a 52% overall yield. A key feature of the synthesis is the high-yielding Ag(I)-catalyzed cycloisomerization of the N-propargylaniline precursor to afford the quinoline carboxylate skeleton from acid-labile methyl aminobenzoate. However, the spectral data of the synthesized aaptoline A were not consistent with those of previous studies. The struc… Show more
“…481 Two different reports from the same authors have called into question the structures proposed for aaptolines A and B, but no alternatives have been provided. 482,483 The structure of njaoamine I has been revised to 1166 following its synthesis using a ring closing alkyne metathesis reaction. 484 Two separate groups have reported the total synthesis of various oxo-aplysinopsin alkaloids.…”
“…481 Two different reports from the same authors have called into question the structures proposed for aaptolines A and B, but no alternatives have been provided. 482,483 The structure of njaoamine I has been revised to 1166 following its synthesis using a ring closing alkyne metathesis reaction. 484 Two separate groups have reported the total synthesis of various oxo-aplysinopsin alkaloids.…”
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