Development of an Artificial Assembly Line Generating Skeletally Diverse Indole Alkaloids Inspired by Biogenetic Strategy
-
- Oguri Hiroki
- Division of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology
Bibliographic Information
- Other Title
-
- 生合成経路を模倣したインドールアルカロイド群の骨格多様化合成
- 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
Search this article
Abstract
<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>
Journal
-
- Journal of Synthetic Organic Chemistry, Japan
-
Journal of Synthetic Organic Chemistry, Japan 74 (9), 854-865, 2016
The Society of Synthetic Organic Chemistry, Japan
- Tweet
Keywords
Details 詳細情報について
-
- CRID
- 1390282680318024320
-
- NII Article ID
- 130005421115
-
- NII Book ID
- AN0024521X
-
- ISSN
- 18836526
- 00379980
-
- NDL BIB ID
- 027631677
-
- Text Lang
- ja
-
- Data Source
-
- JaLC
- NDL
- Crossref
- CiNii Articles
- KAKEN
-
- Abstract License Flag
- Disallowed