Designed whole-cell-catalysis-assisted synthesis of 9,11-secosterols

• Marek Kõllo,
• Marje Kasari,
• Villu Kasari,
• Tõnis Pehk,
• Ivar Järving,
• Margus Lopp,
• Arvi Jõers and
• Tõnis Kanger

Beilstein J. Org. Chem. 2021, 17, 581–588, doi:10.3762/bjoc.17.52

• Tartu, Estonia National Institute of Chemical Physics and Biophysics, Akadeemia tee 23, 12618 Tallinn, Estonia 10.3762/bjoc.17.52 Abstract A method for the synthesis of 9,11-secosteroids starting from the natural corticosteroid cortisol is described. There are two key steps in this approach, combining

• toxic oxidants. Keywords: chemoenzymatic synthesis; cortisol; hydroxylation; secosterol; whole-cell catalysis; Introduction Developments in the chemistry of steroids have stimulated extensive research interest in the exploration of new synthetic methods since the 1960s. Advances in synthetic biology

• 1,2-diols. Starting with a compound already possessing a hydroxy group at the position C11, only hydroxylation at C9 is needed. Commercially available corticosteroid cortisol already possesses a hydroxy group at the position C11, and therefore only hydroxylation at C9 is needed, making cortisol (1) an

Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds

• Vuyisa Mzozoyana,
• Fanie R. van Heerden and
• Craig Grimmer

Beilstein J. Org. Chem. 2020, 16, 190–199, doi:10.3762/bjoc.16.22

• cross-coupling reaction [17], Negishi cross-coupling reaction [18] and Wittig reaction [17]. The concept of the incorporation of fluorine into organic molecules has gained much interest since Fried and Sabo reported the improvement of the therapeutic index of cortisol by the incorporation of a fluorine

Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds

• Victoria V. Lipson,
• Tetiana L. Pavlovska,
• Nataliya V. Svetlichnaya,
• Anna A. Poryvai,
• Nikolay Yu. Gorobets,
• Erik V. Van der Eycken,
• Irina S. Konovalova,
• Svetlana V. Shiskina,
• Alexander V. Borisov,
• Vladimir I. Musatov and
• Alexander V. Mazepa

Beilstein J. Org. Chem. 2019, 15, 1032–1045, doi:10.3762/bjoc.15.101

• (CYP11B2) and 11β-hydroxylase (CYP11B1), which is responsible for cortisol production [35]. This compound is under development for the treatment of Cushing's syndrome and pituitary ACTH hypersecretion [36]. From this point of view the approach to pyrrolo[1,2-c]imidazole moiety by using acyclic methylene

A protecting group-free synthesis of the Colorado potato beetle pheromone

• Zhongtao Wu,
• Manuel Jäger,
• Jeffrey Buter and
• Adriaan J. Minnaard

Beilstein J. Org. Chem. 2013, 9, 2374–2377, doi:10.3762/bjoc.9.273

• pattern in 1 occurs more widespread in natural products and pharmaceuticals such as in cortisol (hydrocortisone). Results and Discussion The synthesis of (S)-1 is summarized in Scheme 3. The choice for either geraniol or nerol should have been based on the stereoselectivity of the Sharpless epoxidation