Enantioselective total synthesis of (−)-pseudophrynaminol through tandem olefination, isomerization and asymmetric Claisen rearrangement |
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Authors: | Tomomi KawasakiAtsuyo Ogawa Yasuyuki TakashimaMasanori Sakamoto |
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Institution: | Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan |
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Abstract: | A new and efficient total synthesis of (−)-pseudophrynaminol, the pyrrolo2,3-b]indole alkaloid bearing the allylic moiety at the 3a-position, has been achieved by a sequence involving 3-allylindol-2-one 8 as a key intermediate. The enantioselective construction of the quaternary carbon in 8 was performed through a tandem cascade reaction of 2-allyloxyindolin-3-one 4, olefination, isomerization, and asymmetric Claisen rearrangement. |
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