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Literature DB >> 15900526

Total synthesis of avrainvillamide (CJ-17,665) and stephacidin B.

Phil S Baran¹, Carlos A Guerrero, Benjamin D Hafensteiner, Narendra B Ambhaikar.

Abstract

Entities: Chemical

Mesh：

Substances：

Year: 2005 PMID： 15900526 DOI： 10.1002/anie.200500655

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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17 in total

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors: K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal: Chem Soc Rev Date: 2012-06-28 Impact factor: 54.564

2. Evidence for the rapid conversion of stephacidin B into the electrophilic monomer avrainvillamide in cell culture.

Authors: Jeremy E Wulff; Seth B Herzon; Romain Siegrist; Andrew G Myers
Journal: J Am Chem Soc Date: 2007-03-31 Impact factor: 15.419

3. Isolation, structure elucidation, and biomimetic total synthesis of versicolamide B, and the isolation of antipodal (-)-stephacidin A and (+)-notoamide B from Aspergillus versicolor NRRL 35600.

Authors: Thomas J Greshock; Alan W Grubbs; Ping Jiao; Donald T Wicklow; James B Gloer; Robert M Williams
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

Review 4. Synthetic approaches to the bicyclo[2.2.2]diazaoctane ring system common to the paraherquamides, stephacidins and related prenylated indole alkaloids.

Authors: Kenneth A Miller; Robert M Williams
Journal: Chem Soc Rev Date: 2009-09-16 Impact factor: 54.564

Total synthesis of avrainvillamide (CJ-17,665) and stephacidin B.

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

2. Evidence for the rapid conversion of stephacidin B into the electrophilic monomer avrainvillamide in cell culture.

3. Isolation, structure elucidation, and biomimetic total synthesis of versicolamide B, and the isolation of antipodal (-)-stephacidin A and (+)-notoamide B from Aspergillus versicolor NRRL 35600.

Review 4. Synthetic approaches to the bicyclo[2.2.2]diazaoctane ring system common to the paraherquamides, stephacidins and related prenylated indole alkaloids.

Review 5. Natural products synthesis: enabling tools to penetrate Nature's secrets of biogenesis and biomechanism.

6. Bioinspired chemical synthesis of monomeric and dimeric stephacidin A congeners.

7. Chemoselectivity: the mother of invention in total synthesis.

8. Oxidative Coupling of Enolates, Enol Silanes and Enamines: Methods and Natural Product Synthesis.

9. Concise, asymmetric, stereocontrolled total synthesis of stephacidins A, B and notoamide B.

10. Direct, chemoselective N-tert-prenylation of indoles by C-H functionalization.