2010年10月
The first total synthesis and structural determination of epi-cochlioquinone A
TETRAHEDRON LETTERS
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- 巻
- 51
- 号
- 42
- 開始ページ
- 5532
- 終了ページ
- 5536
- 記述言語
- 英語
- 掲載種別
- DOI
- 10.1016/j.tetlet.2010.07.153
- 出版者・発行元
- PERGAMON-ELSEVIER SCIENCE LTD
The first total synthesis of epi-cochlioquinone A has been achieved in a highly convergent manner via [3+3] cycloaddition of catechol 2 and oxadecalin 3 as the key reaction. The synthesis of the catechol segment, possessing the side chain with multi stereogenic centers, features the asymmetric vinylogous Mukaiyama aldol reaction, the stereoselective conjugate addition to the nitroalkene, the stereospecific nitro-Dieckmann condensation, and the transformation of 6-nitrocyclohex-2-enone into catechol 2, using two new methodologies, such as (i) the hydrogen-transfer reaction to o-aminophenol and the subsequent auto-redox-catalysis to catechol and (ii) the direct oxidation of 6-nitrocyclohex-2-enone to o-quinone and the subsequent reduction. The oxadecalin segment was synthesized from a glycosyl cyanide by the [3+3] annulation with a ketone and an acetoacetate. These segments were connected by the [3+3] cyclization, and the resulting tetracyclic compound was subjected to a specific oxidation of the protected hydroquinone to provide epi-cochlioquinone A. (C) 2010 Elsevier Ltd. All rights reserved.
- リンク情報
- ID情報
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- DOI : 10.1016/j.tetlet.2010.07.153
- ISSN : 0040-4039
- CiNii Articles ID : 80021368560
- Web of Science ID : WOS:000282734400006