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Stereoselective total synthesis of (±)-homochelidonine

✍ Scribed by Makoto Yoshida; Toshiko Watanabe; Tsutomu Ishikawa

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
86 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

±)-Homochelidonine, a B/C-cis-11-hydroxyhexahydrobenzo[c]phenanthridine alkaloid, was stereoselectively synthesized from arnottin II, a non-alkaloidal spirolactonyl tetralone which had been structurally correlated to chelerythrine, a fully aromatized-type alkaloid, by the common use of a 2-benzofuranyl-1-tetralone as a synthetic key intermediate. Thus, a valuable synthetic method accessible to benzo[c]phenanthridine alkaloids with different oxidation stages of the basic skeleton could be proposed.

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