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Literature DB >> 21955040

Total synthesis and stereochemical revision of acortatarins A and B.

Gangarajula Sudhakar¹, Vilas D Kadam, Shruthi Bayya, Gavinolla Pranitha, Bharatam Jagadeesh.

Abstract

A first total synthesis of acortatarins A, B, and an enantiomer of the proposed structure of acortatarin B is described by using readily available d-sugars. This convergent total synthesis revealed the revision of the absolute configuration of acortatarin A and structural revision of acortatarin B. The key steps involved are regioselective epoxide opening with deprotonated 2,5-disubstituted pyrrole and spiroketalization.

Entities: Chemical Disease

Mesh：

Substances：

Year: 2011 PMID： 21955040 DOI： 10.1021/ol202121k

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

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Cited

8 in total

1. Stereoselective synthesis of acortatarins A and B.

Authors: Jacqueline M Wurst; Alyssa L Verano; Derek S Tan
Journal: Org Lett Date: 2012-08-27 Impact factor: 6.005

2. Stereocontrolled Synthesis of Spiroketals: An Engine for Chemical and Biological Discovery.

Authors: Alyssa L Verano; Derek S Tan
Journal: Isr J Chem Date: 2017-03-10 Impact factor: 3.333

3. Cascade N-Alkylation/Hemiacetalization for Facile Construction of the Spiroketal Skeleton of Acortatarin Alkaloids with Therapeutic Potentiality in Diabetic Nephropathy.

Authors: Pei Cao; Zhen-Jie Li; Wen-Wu Sun; Shashwat Malhotra; Yuan-Liang Ma; Bin Wu; Virinder S Parmar
Journal: Nat Prod Bioprospect Date: 2014-12-16

4. Family-level stereoselective synthesis and biological evaluation of pyrrolomorpholine spiroketal natural product antioxidants.

Authors: Alyssa L Verano; Derek S Tan
Journal: Chem Sci Date: 2017-03-15 Impact factor: 9.825

5. Synthesis, Structural Studies, and α-Glucosidase Inhibitory, Antidiabetic, and Antioxidant Activities of 2,3-Dihydroquinazolin-4(1H)-ones Derived from Pyrazol-4-carbaldehyde and Anilines.

Authors: Alireza Barmak; Khodabakhsh Niknam; Gholamhossein Mohebbi
Journal: ACS Omega Date: 2019-10-25

Total synthesis and stereochemical revision of acortatarins A and B.

1. Stereoselective synthesis of acortatarins A and B.

2. Stereocontrolled Synthesis of Spiroketals: An Engine for Chemical and Biological Discovery.

3. Cascade N-Alkylation/Hemiacetalization for Facile Construction of the Spiroketal Skeleton of Acortatarin Alkaloids with Therapeutic Potentiality in Diabetic Nephropathy.

4. Family-level stereoselective synthesis and biological evaluation of pyrrolomorpholine spiroketal natural product antioxidants.

5. Synthesis, Structural Studies, and α-Glucosidase Inhibitory, Antidiabetic, and Antioxidant Activities of 2,3-Dihydroquinazolin-4(1H)-ones Derived from Pyrazol-4-carbaldehyde and Anilines.

6. Alkaloids isolated from the lateral root of Aconitum carmichaelii.

7. Chemical Constituents from the Stems of Tinospora sinensis and Their Bioactivity.

8. Identification of a Novel Pyrrole Alkaloid from the Edible Mushroom Basidiomycetes-X (Echigoshirayukidake).