A novel route for the construction of Taxol ABC-ring framework: skeletal rearrangement approach to AB-ring and intramolecular aldol approach to C-ring |
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Authors: | Terumichi Enomoto Mifuyu Ueno Yumi Shimada Ryuichi Shirai Kiyomi Kakiuchi |
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Institution: | a Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara 630-0192, Japan b Faculty of Pharmaceutical Sciences, Doshisha Women's College of Liberal Arts, Kodo, Kyotanabe, Kyoto 610-0395, Japan |
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Abstract: | We report here on the construction of the ABC-ring framework of (±)-Taxol using an intramolecular aldol reaction as a key step. AB-ring compound 8 was converted to ketoaldehyde 25 as a precursor of an aldol reaction via introduction of oxygen-functionalities and a methoxycarbonyl group, which can be converted to a methyl group, in the proper positions of the B-ring. An aldol reaction of ketoaldehyde with LDA led to the formation of the desired product 27, which corresponds to the ABC-ring framework of (±)-Taxol. |
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