Literature DB >> 21510628

Total synthesis of (-)-sessilifoliamide C and (-)-8-epi-stemoamide.

Adam T Hoye1, Peter Wipf.   

Abstract

A convergent route featuring [3,3]-sigmatropic rearrangements of a linchpin azepinopyrrolidine served to install two of the four contiguous stereocenters present in the tricyclic Stemona alkaloids sessilifoliamide and stemoamide. In addition to the first total synthesis of (-)-sessilifoliamide C, a potential biosynthetic relationship between the sessilifoliamides and previously reported Stemona alkaloids is presented.

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Year:  2011        PMID： 21510628      PMCID： PMC3099051          DOI： 10.1021/ol200743u

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


  19 in total

Review 1.  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

2.  Synthesis of (-)-9,10-epi-stemoamide.

Authors:  Seock-Kyu Khim; Arthur G Schultz
Journal:  J Org Chem       Date:  2004-10-29       Impact factor: 4.354

3.  Bioinspired and concise synthesis of (±)-stemoamide.

Authors:  Yan Wang; Lili Zhu; Yuying Zhang; Ran Hong
Journal:  Angew Chem Int Ed Engl       Date:  2011-02-17       Impact factor: 15.336

4.  Total synthesis of (±)-maistemonine and (±)-stemonamide.

Authors:  Zhi-Hua Chen; Yong-Qiang Zhang; Zhi-Min Chen; Yong-Qiang Tu; Fu-Min Zhang
Journal:  Chem Commun (Camb)       Date:  2010-12-01       Impact factor: 6.222

5.  Synthesis of (-)-stemoamide using a stereoselective anti-aldol step.

Authors:  Horacio F Olivo; Ricardo Tovar-Miranda; Efraín Barragán
Journal:  J Org Chem       Date:  2006-04-14       Impact factor: 4.354

6.  Stereoselective synthesis of the C(1)-C(12) segment of iriomoteolide 1a: a very potent macrolide antitumor agent.

Authors:  Arun K Ghosh; Hao Yuan
Journal:  Tetrahedron Lett       Date:  2009-04-01       Impact factor: 2.415

7.  Computational study of factors controlling the boat and chair transition states of Ireland-Claisen rearrangements.

Authors:  Seref Gül; Franziska Schoenebeck; Viktorya Aviyente; K N Houk
Journal:  J Org Chem       Date:  2010-03-19       Impact factor: 4.354

8.  Enantioselective total synthesis of (+)-largazole, a potent inhibitor of histone deacetylase.

Authors:  Arun K Ghosh; Sarang Kulkarni
Journal:  Org Lett       Date:  2008-07-29       Impact factor: 6.005

9.  Total synthesis of (-)-stemoamide.

Authors:  Staffan Torssell; Emil Wanngren; Peter Somfai
Journal:  J Org Chem       Date:  2007-04-24       Impact factor: 4.354

Review 10.  Structural relationships, distribution and biological activities of stemona alkaloids.

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

1.  A versatile enantioselective synthesis of azabicyclic ring systems: a concise total synthesis of (+)-grandisine D and unnatural analogues.

Authors:  Olugbeminiyi O Fadeyi; Timothy J Senter; Kristopher N Hahn; Craig W Lindsley
Journal:  Chemistry       Date:  2012-03-30       Impact factor: 5.236

2.  A General, Enantioselective Synthesis of 1-Azabicyclo[m.n.0]alkane Ring Systems.

Authors:  Timothy J Senter; Michael L Schulte; Leah C Konkol; Tyler E Wadzinski; Craig W Lindsley
Journal:  Tetrahedron Lett       Date:  2013-03-27       Impact factor: 2.415
  2 in total

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