Literature DB >> 12492320

A highly stereoselective asymmetric synthesis of (--)-lobeline and (--)-sedamine.

François-Xavier Felpin1, Jacques Lebreton.   

Abstract

A highly stereoselective asymmetric synthesis of (--)-sedamine and (--)-lobeline is described from benzaldehyde in 16 and 17 steps with an overall yield of 20% and 14%, respectively. The key intermediate syn-3,4-epoxyalcohol was prepared in a highly diastereomeric fashion (>99% ee, dr) and served as a common intermediate for both alkaloids.

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Year:  2002        PMID： 12492320     DOI： 10.1021/jo020501y

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  8 in total

1.  Pd-catalyzed enantioselective aerobic oxidation of secondary alcohols: applications to the total synthesis of alkaloids.

Authors:  Shyam Krishnan; Jeffrey T Bagdanoff; David C Ebner; Yeeman K Ramtohul; Uttam K Tambar; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2008-09-18       Impact factor: 15.419

Review 2.  Design, synthesis and interaction at the vesicular monoamine transporter-2 of lobeline analogs: potential pharmacotherapies for the treatment of psychostimulant abuse.

Authors:  Peter A Crooks; Guangrong Zheng; Ashish P Vartak; John P Culver; Fang Zheng; David B Horton; Linda P Dwoskin
Journal:  Curr Top Med Chem       Date:  2011       Impact factor: 3.295

3.  Novel approach to multifunctionalized homoallylic alcohols via regioselective ring opening of aryl oxiranes with 3-iodo allenoates.

Authors:  Adiseshu Kattuboina; Parminder Kaur; Cody Timmons; Guigen Li
Journal:  Org Lett       Date:  2006-06-22       Impact factor: 6.005

4.  C6-C8 bridged epothilones: consequences of installing a conformational lock at the edge of the macrocycle.

Authors:  Weiqiang Zhan; Yi Jiang; Shubhada Sharma; Peggy J Brodie; Susan Bane; David G I Kingston; Dennis C Liotta; James P Snyder
Journal:  Chemistry       Date:  2011-11-30       Impact factor: 5.236

5.  Synthesis of Lobeline, Lobelane and their Analogues. A Review.

Authors:  Guangrong Zheng; Peter A Crooks
Journal:  Org Prep Proced Int       Date:  2015-08-17       Impact factor: 1.628

6.  Mannich-type Reactions of Cyclic Nitrones: Effective Methods for the Enantioselective Synthesis of Piperidine-containing Alkaloids.

Authors:  Vladislav G Lisnyak; Tessa Lynch-Colameta; Scott A Snyder
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-19       Impact factor: 15.336

7.  Indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline: application to the synthesis of (-)-sedamine.

Authors:  Guangrong Zheng; Linda P Dwoskin; Peter A Crooks
Journal:  J Org Chem       Date:  2004-11-26       Impact factor: 4.354

8.  Diversification of Unprotected Alicyclic Amines by C-H Bond Functionalization: Decarboxylative Alkylation of Transient Imines.

Authors:  Anirudra Paul; Jae Hyun Kim; Scott D Daniel; Daniel Seidel
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-17       Impact factor: 15.336
  8 in total

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