Literature DB >> 22987285

Enantioselective formal total syntheses of didehydrostemofoline and isodidehydrostemofoline through a catalytic dipolar cycloaddition cascade.

Chao Fang1, Charles S Shanahan, Daniel H Paull, Stephen F Martin.   

Abstract

Sweet to the core: Enantioselective formal total syntheses of the title compounds were accomplished in 24 steps from 2-deoxy-D-ribose. The synthesis features a novel cascade of reactions culminating in an intramolecular dipolar cycloaddition to form the tricyclic core of the stemofoline alkaloids from an acyclic diazo imine intermediate.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID： 22987285      PMCID： PMC3541778          DOI： 10.1002/anie.201205274

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


  22 in total

1.  Novel Entry to the Tricyclic Core of Stemofoline and Didehydrostemofoline.

Authors:  Jochen Dietz; Stephen F Martin
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

Review 2.  The chemistry of Stemona alkaloids: An update.

Authors:  Ronaldo Aloise Pilli; Giovanni Bernardi Rosso; Maria da Conceição Ferreira de Oliveira
Journal:  Nat Prod Rep       Date:  2010-11-02       Impact factor: 13.423

3.  Alkaloids from the roots of Stemona aphylla.

Authors:  Pitchaya Mungkornasawakul; Sukanda Chaiyong; Thanapat Sastraruji; Araya Jatisatienr; Chaiwat Jatisatienr; Stephen G Pyne; Alison T Ung; John Korth; Wilford Lie
Journal:  J Nat Prod       Date:  2009-05-22       Impact factor: 4.050

4.  Biochemical mechanism of modulation of human P-glycoprotein by stemofoline.

Authors:  Wisinee Chanmahasathien; Shinobu Ohnuma; Suresh V Ambudkar; Pornngarm Limtrakul
Journal:  Planta Med       Date:  2011-07-22       Impact factor: 3.352

5.  Reducing the cost, smell, and toxicity of the Barton reductive decarboxylation: chloroform as the hydrogen atom source.

Authors:  Eun Jung Ko; G Paul Savage; Craig M Williams; John Tsanaktsidis
Journal:  Org Lett       Date:  2011-03-25       Impact factor: 6.005

6.  Semisynthesis and acetylcholinesterase inhibitory activity of stemofoline alkaloids and analogues.

Authors:  Kwankamol Sastraruji; Thanapat Sastraruji; Stephen G Pyne; Alison T Ung; Araya Jatisatienr; Wilford Lie
Journal:  J Nat Prod       Date:  2010-05-28       Impact factor: 4.050

7.  Synthetic approaches to the polycyclic alkaloid stemofoline.

Authors:  Alison M Baylis; Michael P H Davies; Eric J Thomas
Journal:  Org Biomol Chem       Date:  2007-08-14       Impact factor: 3.876

Review 8.  Structural relationships, distribution and biological activities of stemona alkaloids.

Authors:  Harald Greger
Journal:  Planta Med       Date:  2006-02       Impact factor: 3.352

9.  Application of an intramolecular dipolar cycloaddition to an asymmetric synthesis of the fully oxygenated tricyclic core of the stemofoline alkaloids.

Authors:  Ryan J Carra; Matthew T Epperson; David Y Gin
Journal:  Tetrahedron       Date:  2008-04-21       Impact factor: 2.457

10.  Semisynthesis and biological activity of stemofoline alkaloids.

Authors:  Morwenna C Baird; Stephen G Pyne; Alison T Ung; Wilford Lie; Thanapat Sastraruji; Araya Jatisatienr; Chaiwat Jatisatienr; Srisulak Dheeranupattana; Jaturong Lowlam; Sukanya Boonchalermkit
Journal:  J Nat Prod       Date:  2009-04       Impact factor: 4.050
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  8 in total

1.  Diastereoselective addition of monoorganocuprates to a chiral fumarate: reaction development and synthesis of (-)-dihydroprotolichesterinic acid.

Authors:  J Caleb Hethcox; Charles S Shanahan; Stephen F Martin
Journal:  Tetrahedron       Date:  2015-09-16       Impact factor: 2.457

2.  Natural Products and Their Mimics as Targets of Opportunity for Discovery.

Authors:  Stephen F Martin
Journal:  J Org Chem       Date:  2017-09-15       Impact factor: 4.354

3.  Total Syntheses of Bisdehydroneostemoninine and Bisdehydrostemoninine by Catalytic Carbonylative Spirolactonization.

Authors:  Kaiqing Ma; Xianglin Yin; Mingji Dai
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-18       Impact factor: 15.336

4.  Hydrodecarboxylation of Carboxylic and Malonic Acid Derivatives via Organic Photoredox Catalysis: Substrate Scope and Mechanistic Insight.

Authors:  Jeremy D Griffin; Mary A Zeller; David A Nicewicz
Journal:  J Am Chem Soc       Date:  2015-08-28       Impact factor: 15.419

5.  Nickel-Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms.

Authors:  Tian Qin; Lara R Malins; Jacob T Edwards; Rohan R Merchant; Alexander J E Novak; Jacob Z Zhong; Riley B Mills; Ming Yan; Changxia Yuan; Martin D Eastgate; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-16       Impact factor: 15.336

6.  Rapid synthesis of bicyclic lactones via palladium-catalyzed aminocarbonylative lactonizations.

Authors:  Xianglin Yin; Haroon Mohammad; Hassan E Eldesouky; Ahmed Abdelkhalek; Mohamed N Seleem; Mingji Dai
Journal:  Chem Commun (Camb)       Date:  2017-06-29       Impact factor: 6.222

7.  Asymmetric Formal Total Synthesis of the Stemofoline Alkaloids: The Evolution, Development and Application of a Catalytic Dipolar Cycloaddition Cascade.

Authors:  Charles S Shanahan; Chao Fang; Daniel H Paull; Stephen F Martin
Journal:  Tetrahedron       Date:  2013-09-09       Impact factor: 2.457

8.  Diazoacetoacetate enones for the synthesis of diverse natural product-like scaffolds.

Authors:  Charles S Shanahan; Phong Truong; Savannah M Mason; John S Leszczynski; Michael P Doyle
Journal:  Org Lett       Date:  2013-07-05       Impact factor: 6.005
  8 in total

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