A novel route for the construction of Taxol ABC-ring framework: skeletal rearrangement approach to AB-ring and intramolecular aldol approach to C-ring

Enomoto T; Morimoto T; Ueno M; Matsukubo T; Shimada Y; Tsutsumi K; Shirai R; Kakiuchi K

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A novel route for the construction of Taxol ABC-ring framework: skeletal rearrangement approach to AB-ring and intramolecular aldol approach to C-ring

机译：构建紫杉酚ABC环骨架的新途径：AB环的骨架重排方法和C环的分子内羟醛方法

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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 methoxycarbony] 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. (c) 2008 Elsevier Ltd. All rights reserved.

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《Tetrahedron》 |2008年第18期|共9页
作者
Enomoto T; Morimoto T; Ueno M; Matsukubo T; Shimada Y; Tsutsumi K; Shirai R; Kakiuchi K;
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正文语种 eng
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ENANTIOSELECTIVE TOTAL-SYNTHESIS; ASYMMETRIC TOTAL-SYNTHESIS; 1ST TOTAL-SYNTHESIS; STEREOCONTROLLED SYNTHESIS; NATURAL-PRODUCTS; PINENE PATH; CHEMISTRY; TAXANES; COMPLETION; PACLITAXEL;

机译：对映选择性全合成;不对称全合成;第一全合成;立体合成;天然产物;ENE键路径;化学性质;紫杉烷;完成;PACXITAXEL;

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1. A novel route for the construction of Taxol ABC-ring framework: skeletal rearrangement approach to AB-ring and intramolecular aldol approach to C-ring [J] . Enomoto T, Morimoto T, Ueno M, Tetrahedron . 2008,第18期

机译：构建紫杉酚ABC环骨架的新途径：AB环的骨架重排方法和C环的分子内羟醛方法
2. Tandem intramolecular Michael-aldol reaction as a tool for the construction of the C-ring of hexacyclinic acid [J] . Stelmakh A, Stellfeld T, Kalesse M Organic letters . 2006,第16期

机译：串联分子内迈克尔-羟醛反应作为构建六环素酸C环的工具
3. Tandem intramolecular Michael-aldol reaction as a tool for the construction of the C-ring of hexacyclinic acid [J] . Stelmakh A, Stellfeld T, Kalesse M Organic letters . 2006,第16期

机译：串联分子内迈克尔-羟醛反应作为构建六环素酸C环的工具
4. A segment rearrangement approach to channel routing under the crosstalk constraints [C] . Kyoung-Son Jhang, Soonhoi Ha . 1994

机译：串扰约束下的通道路由分段重排方法
5. I. Photochemical catalytic [6pi + 2pi] higher-order cycloadditions. II. Toward the development of a chiral catalyst for chromium(0) higher-order cycloadditions. III. Synthetic studies toward a synthesis of taxol: Investigation of an intramolecular cycloaddition approach to the taxane core. [D] . Mann, Larry W. 2002

机译：I.光化学催化的[6pi + 2pi]高阶环加成。二。走向手性催化剂的铬（0）高阶环加成反应的发展。三，合成紫杉醇的合成研究：紫杉烷核心分子内环加成方法的研究。
6. Construction of the 12-Dialkenylcyclohexane Framework via Ireland-Claisen Rearrangement and Intramolecular Barbier Reaction: Application to the Synthesis of (±)-Geijerone and a Diastereoisomeric Mixture with Its 5-Epimer [O] . Dawei Liang, Nana Gao, Wei Liu, 2014

机译：通过爱尔兰-克莱森重排和分子内Barbier反应构建12-二烯基环己烷骨架：在合成（±）-Geijerone和其5-表异构体的非对映异构体混合物中的应用
7. Construction of AB-Ring System of Taxane Framework by A-Ring Annulation Strategy: Synthesis of 1-Hydroxy-8,11,11-trimethylbicyclo-(5.3.1)undec-7-en-9-one by Way of Intramolecular Aldol Cyclization to Form the C1-C10 Bond. [O] . Koji YAMADA, Hayato IWADARE, Teruaki MUKAIYAMA 1997

机译：A-Ring Annrulation策略构建紫杉烷框架的Ab-Ring系统：通过分子内醛醇环化合成1-羟基-8,11,111-11-三甲基二甲基二甲基二甲基 - （5.3.1）UNDEC-7-ZH-9-形成C1-C10键。

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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