Literature DB >> 19294722

Total synthesis of ouabagenin and ouabain.

Maddi Sridhar Reddy1, Hongxing Zhang, Serge Phoenix, Pierre Deslongchamps.   

Abstract

A full account of the total synthesis of ouabagenin and ouabain is described. A highly stereocontrolled anionic cycloaddition for the rapid construction of the basic steroid skeleton is a pivotal conversion for the whole strategy. A careful study was needed to establish the order and the sequence of functional group manipulations. Specific conformational features of the ouabain skeleton allowed us to overcome a few stereochemical problems. Degradation studies on ouabain provided an ultimate proof for a key intermediate, which is used as a relay. Late stage butenolide formation and glycosidation yielded ouabain.

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Year:  2009        PMID： 19294722     DOI： 10.1002/asia.200800429

Source DB:  PubMed          Journal:  Chem Asian J        ISSN： 1861-471X


  11 in total

1.  Modular Total Synthesis and Cell-Based Anticancer Activity Evaluation of Ouabagenin and Other Cardiotonic Steroids with Varying Degrees of Oxygenation.

Authors:  Hem Raj Khatri; Bijay Bhattarai; Will Kaplan; Zhongzheng Li; Marcus John Curtis Long; Yimon Aye; Pavel Nagorny
Journal:  J Am Chem Soc       Date:  2019-03-14       Impact factor: 15.419

2.  Recent Progress in Steroid Synthesis Triggered by the Emergence of New Catalytic Methods.

Authors:  Hem Raj Khatri; Nolan Carney; Ryan Rutkoski; Bijay Bhattarai; Pavel Nagorny
Journal:  European J Org Chem       Date:  2020-01-01

3.  Regioselective single pot C3-glycosylation of strophanthidol using methylboronic acid as a transient protecting group.

Authors:  Jia-Hui Tay; Valentin Dorokhov; Sibin Wang; Pavel Nagorny
Journal:  J Antibiot (Tokyo)       Date:  2019-04-04       Impact factor: 2.649

4.  Concise Enantioselective Total Synthesis of Cardiotonic Steroids 19-Hydroxysarmentogenin and Trewianin Aglycone.

Authors:  Will Kaplan; Hem Raj Khatri; Pavel Nagorny
Journal:  J Am Chem Soc       Date:  2016-05-27       Impact factor: 15.419

5.  Asymmetric synthesis of dihydroindanes by convergent alkoxide-directed metallacycle-mediated bond formation.

Authors:  Stephen N Greszler; Holly A Reichard; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2012-01-31       Impact factor: 15.419

6.  Synthetic studies on the indane SHIP1 agonist AQX-1125.

Authors:  Otto M Dungan; Shawn Dormann; Sandra Fernandes; Brian C Duffy; Daniel G Effiong; William G Kerr; John D Chisholm
Journal:  Org Biomol Chem       Date:  2022-05-18       Impact factor: 3.890

7.  Concise Enantioselective Synthesis of Oxygenated Steroids via Sequential Copper(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions.

Authors:  Nathan R Cichowicz; Will Kaplan; Yaroslav Khomutnyk; Bijay Bhattarai; Zhankui Sun; Pavel Nagorny
Journal:  J Am Chem Soc       Date:  2015-11-10       Impact factor: 15.419

8.  Enantioselective Total Synthesis of Cannogenol-3-O-α-l-rhamnoside via Sequential Cu(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions.

Authors:  Bijay Bhattarai; Pavel Nagorny
Journal:  Org Lett       Date:  2017-12-15       Impact factor: 6.005

9.  Development of a concise synthesis of ouabagenin and hydroxylated corticosteroid analogues.

Authors:  Hans Renata; Qianghui Zhou; Georg Dünstl; Jakob Felding; Rohan R Merchant; Chien-Hung Yeh; Phil S Baran
Journal:  J Am Chem Soc       Date:  2015-01-16       Impact factor: 15.419

10.  Site-Selective Acylations with Tailor-Made Catalysts.

Authors:  Florian Huber; Stefan F Kirsch
Journal:  Chemistry       Date:  2016-03-10       Impact factor: 5.236
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