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Literature DB >> 12917000

Concise, asymmetric total synthesis of spirotryprostatin A.

Tomoyuki Onishi¹, Paul R Sebahar, Robert M Williams.

Abstract

[structure: see text] The structurally intriguing cell-cycle inhibitor spirotryprostatin A has been synthesized utilizing an azomethine ylide dipolar cycloaddition reaction as the key step. This pentacyclic alkaloid contains a prenylated tryptophan-derived oxindole moiety that has been created in a regiocontrolled and stereocontrolled manner in a single step.

Entities: Chemical

Mesh：

Substances：

Year: 2003 PMID： 12917000 DOI： 10.1021/ol0351910

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

12 in total

1. Synthetic Studies on Palau'amine. Construction of the Cyclopentane Core via an Asymmetric 1,3-Dipolar Cycloaddition.

Authors: Kosuke Namba; Makto Inai; Uta Sundermeier; Thomas J Greshock; Robert M Williams
Journal: Tetrahedron Lett Date: 2010-12-15 Impact factor: 2.415

Review 2. Natural products synthesis: enabling tools to penetrate Nature's secrets of biogenesis and biomechanism.

Authors: Robert M Williams
Journal: J Org Chem Date: 2011-04-12 Impact factor: 4.354

3. New Tricks in Amino Acid Synthesis: Applications to Complex Natural Products.

Authors: Robert M Williams; Cameron M Burnett
Journal: ACS Symp Ser Am Chem Soc Date: 2009-06-14

4. Three-Component [3+2] Cycloaddition for Regio- and Diastereoselective Synthesis of Spirooxindole-Pyrrolidines.

Authors: Xiaofeng Zhang; Miao Liu; Desheng Zhan; Manpreet Kaur; Jerry P Jasinski; Wei Zhang
Journal: New J Chem Date: 2022-01-20 Impact factor: 3.925

5. A Diastereoselective Intramolecular Pauson-Khand Approach to the Construction of the BC Ring System in Tuberostemoninol.

Authors: Xiangna Jia; Robert M Williams
Journal: Tetrahedron Asymmetry Date: 2008-12-12

10. Secondary Metabolites and Biological Activities of Talaromyces sp. LGT-2, an Endophytic Fungus from Tripterygium Wilfordii.

Authors: Qiu-Hong Zhao; Zhong-Duo Yang; Zong-Mei Shu; Yong-Gang Wang; Ming-Gang Wang
Journal: Iran J Pharm Res Date: 2016 Impact factor: 1.696

Concise, asymmetric total synthesis of spirotryprostatin A.

1. Synthetic Studies on Palau'amine. Construction of the Cyclopentane Core via an Asymmetric 1,3-Dipolar Cycloaddition.

Review 2. Natural products synthesis: enabling tools to penetrate Nature's secrets of biogenesis and biomechanism.

3. New Tricks in Amino Acid Synthesis: Applications to Complex Natural Products.

4. Three-Component [3+2] Cycloaddition for Regio- and Diastereoselective Synthesis of Spirooxindole-Pyrrolidines.

5. A Diastereoselective Intramolecular Pauson-Khand Approach to the Construction of the BC Ring System in Tuberostemoninol.

6. Multicomponent reaction discovery: three-component synthesis of spirooxindoles.

7. (3R,8aS)-3-Ethyl-perhydro-pyrrolo[1,2-a]pyrazine-1,4-dione.

8. SYNTHETIC STUDIES ON MPC1001: A DIPOLAR CYCLOADDITION APPROACH TO THE PYRROLIDINE RING SYSTEM.

9. Expanding the chemical diversity of spirooxindoles via alkylative pyridine dearomatization.

10. Secondary Metabolites and Biological Activities of Talaromyces sp. LGT-2, an Endophytic Fungus from Tripterygium Wilfordii.