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Literature DB >> 17685535

Chemoenzymatic approaches to lycorine-type Amaryllidaceae alkaloids: total syntheses of ent-lycoricidine, 3-epi-ent-lycoricidine, and 4-deoxy-3-epi-ent-lycoricidine.

Maria Matveenko¹, Okanya J Kokas, Martin G Banwell, Anthony C Willis.

Abstract

The readily available and enzymatically derived cis-1,2-dihydrocatechol 4 has been elaborated, over 11 steps including an Overman rearrangement, into the non-natural enantiomer, (-)-1, of the alkaloid lycoricidine [(+)-1]. Related chemistries have provided analogues 18, 19, and 26.

Entities: Chemical

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Year: 2007 PMID： 17685535 DOI： 10.1021/ol701552r

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

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Cited

7 in total

1. Chemoenzymatic synthesis of Amaryllidaceae constituents and biological evaluation of their C-1 analogues. The next generation synthesis of 7-deoxypancratistatin and trans-dihydrolycoricidine.

Authors: Jonathan Collins; Uwe Rinner; Michael Moser; Tomas Hudlicky; Ion Ghiviriga; Anntherese E Romero; Alexander Kornienko; Dennis Ma; Carly Griffin; Siyaram Pandey
Journal: J Org Chem Date: 2010-05-07 Impact factor: 4.354

2. Enantioselective Synthesis of Isocarbostyril Alkaloids and Analogs Using Catalytic Dearomative Functionalization of Benzene.

Authors: Tanner W Bingham; Lucas W Hernandez; Daniel G Olson; Riley L Svec; Paul J Hergenrother; David Sarlah
Journal: J Am Chem Soc Date: 2018-12-20 Impact factor: 15.419

Chemoenzymatic approaches to lycorine-type Amaryllidaceae alkaloids: total syntheses of ent-lycoricidine, 3-epi-ent-lycoricidine, and 4-deoxy-3-epi-ent-lycoricidine.

1. Chemoenzymatic synthesis of Amaryllidaceae constituents and biological evaluation of their C-1 analogues. The next generation synthesis of 7-deoxypancratistatin and trans-dihydrolycoricidine.

2. Enantioselective Synthesis of Isocarbostyril Alkaloids and Analogs Using Catalytic Dearomative Functionalization of Benzene.

3. Palladium-catalyzed synthesis of 9-fluorenylidenes through aryne annulation.

4. Total Synthesis of Lycoricidine and Narciclasine by Chemical Dearomatization of Bromobenzene.

Review 5. The role of biocatalysis in the asymmetric synthesis of alkaloids.

6. Short, enantioselective, gram-scale synthesis of (-)-zephyranthine.

7. Stereoselective synthesis of trans-dihydronarciclasine derivatives containing a 1,4-benzodioxane moiety.