- Total Syntheses of (-)-Mersicarpine, (-)-Scholarisine G, (+)-Melodinine E, (-)-Leuconoxine, (-)-Leuconolam, (-)-Leuconodine A, (+)-Leuconodine F, and (-)-Leuconodine C: Self-Induced Diastereomeric Anisochronism (SIDA) Phenomenon for Scholarisine G and Leu
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(Chemical Equation Presented) Enantioselective total syntheses of title natural products from a common cyclohexenone derivative (S)-18 were reported. Ozonolysis of (S)-18 afforded a stable diketo ester (R)-17 that was subsequently converted to two skeleta
- Xu, Zhengren,Wang, Qian,Zhu, Jieping
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supporting information
p. 6712 - 6724
(2015/06/08)
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- Transformations of the 2,7- Seco Aspidosperma alkaloid leuconolam, structure revision of epi -leuconolam, and partial syntheses of leuconoxine and leuconodines A and F
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Several transformations of the seco Aspidosperma alkaloid leuconolam were carried out. The based-induced reaction resulted in cyclization to yield two epimers, the major product corresponding to the optical antipode of a (+)-meloscine derivative. The structures and relative configuration of the products were confirmed by X-ray diffraction analysis. Reaction of leuconolam and epi-leuconolam with various acids, molecular bromine, and hydrogen gave results that indicated that the structure of the alkaloid, previously assigned as epi-leuconolam, was incorrect. This was confirmed by an X-ray diffraction analysis, which revealed that epi-leuconolam is in fact 6,7-dehydroleuconoxine. Short partial syntheses of the diazaspiro indole alkaloid leuconoxine and the new leuconoxine-type alkaloids leuconodines A and F were carried out.
- Low, Yun-Yee,Hong, Fong-Jiao,Lim, Kuan-Hon,Thomas, Noel F.,Kam, Toh-Seok
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p. 327 - 338
(2014/03/21)
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