書誌事項
- タイトル別名
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- Development of an Artificial Assembly Line Generating Skeletally Diverse Indole Alkaloids Inspired by Biogenetic Strategy
- セイゴウセイ ケイロ オ モホウ シタ インドールアルカロイドグン ノ コッカク タヨウカ ゴウセイ
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<p>With intention to formulate a potentially general synthetic strategy generating a collection of skeletally diverse scaffolds without simplifying a structural feature of natural products, we devised an artificial assembly line of terpenoid indole alkaloids and its variants. Inspired by the key biosynthetic intermediate, dehydrosecodine, responsible for divergent intramolecular cyclizations, a “multipotent intermediate” with improved stability and versatile reactivity was designed to establish a streamlined divergent synthetic process. A newly developed copper-catalyzed cyclization protocol allowed rapid formation of the sensitive dihydropyridine system. By harnessing the versatile reactivity of the multipotent intermediate, three types of bioinspired [4+2] cycloadditions as well as two types of oxidation-triggered cyclizations were successfully implemented to generate five distinct scaffolds involving iboga-, aspidosperma-, andranginine- and ngouniensine-type skeletons and unnatural tetracyclic framework within 6-9 steps from tryptamine. Furthermore, simple manipulations of the [4+2] products allowed total synthesis of (−)-catharanthine, (±)-vincadifformine and (±)-andranginine, demonstrating a structural relevance of our compound collections to the natural products.</p>
収録刊行物
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- 有機合成化学協会誌
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有機合成化学協会誌 74 (9), 854-865, 2016
公益社団法人 有機合成化学協会
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詳細情報 詳細情報について
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- CRID
- 1390282680318024320
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- NII論文ID
- 130005421115
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- NII書誌ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 027631677
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- 本文言語コード
- ja
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- データソース種別
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- 使用不可