(±)-ヘデラシンBの全合成研究 [in Japanese] Synthetic Studies on (+/-)-Hederacine B [in Japanese]
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Hederacines A and B, isolated from Glechoma hederaceae L. in 2003, are structurally unique alkaloids, which show moderate levels of cytotoxicity against colon cancer cell line. We have previously reported the synthesis of the functionalized 5-6-5-fused azatricyclic hemiaminal, a potential intermediate in the total synthesis of hederacines, in 33 steps from 2-methyl-1,3-cyclopentanedione, involving an allylic cyanate-to-isocyanate rearrangement, ene-yne ring closing metathesis, and a transannular reaction between the C-5 amino group and the C-12 position of the 5-amino-perhydroazuleno[5,6-b]furanone derivative. This poster presentation will present the progress of our work toward the synthesis of hederacine B via stereoselective introduction of the amino group at C-9 of the azatricyclic hemiaminal intermediate.
- Proceedings of the Symposium on Progress in Organic Reactions and Syntheses
Proceedings of the Symposium on Progress in Organic Reactions and Syntheses 35(0), 100-100, 2009
Division of Organic Chemistry, The Pharmaceutical Society of Japan