Literature DB >> 11869109

Total synthesis of (+/-)-jamtine using a thionium/N-acyliminium ion cascade.

Albert Padwa1, M Diana Danca.   

Abstract

[reaction: see text] The first total synthesis of (+/-)-jamtine (4), a tetrahydroisoquinoline alkaloid reputed for its therapeutic properties, is described. The key step involves a tandem thionium/N-acyliminium ion cyclization from enamido sulfoxide 13. The cascade process takes place with high diastereoselectivity and in excellent yield.

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Year:  2002        PMID： 11869109     DOI： 10.1021/ol017193v

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


  5 in total

1.  Structure-activity relationships at the 5-position of thiolactomycin: an intact (5R)-isoprene unit is required for activity against the condensing enzymes from Mycobacterium tuberculosis and Escherichia coli.

Authors:  Pilho Kim; Yong-Mei Zhang; Gautham Shenoy; Quynh-Anh Nguyen; Helena I Boshoff; Ujjini H Manjunatha; Michael B Goodwin; John Lonsdale; Allen C Price; Darcie J Miller; Ken Duncan; Stephen W White; Charles O Rock; Clifton E Barry; Cynthia S Dowd
Journal:  J Med Chem       Date:  2006-01-12       Impact factor: 7.446

2.  The Domino Way to Heterocycles.

Authors:  Albert Padwa; Scott K Bur
Journal:  Tetrahedron       Date:  2007-06-18       Impact factor: 2.457

3.  Short, enantioselective total syntheses of (-)-8-demethoxyrunanine and (-)-cepharatines A, C, and D.

Authors:  Kangway V Chuang; Raul Navarro; Sarah E Reisman
Journal:  Angew Chem Int Ed Engl       Date:  2011-08-30       Impact factor: 15.336

Review 4.  Application of the Asymmetric Pictet-Spengler Reaction in the Total Synthesis of Natural Products and Relevant Biologically Active Compounds.

Authors:  Majid M Heravi; Vahideh Zadsirjan; Masumeh Malmir
Journal:  Molecules       Date:  2018-04-18       Impact factor: 4.411

Review 5.  The Pictet-Spengler Reaction Updates Its Habits.

Authors:  Andrea Calcaterra; Laura Mangiardi; Giuliano Delle Monache; Deborah Quaglio; Silvia Balducci; Simone Berardozzi; Antonia Iazzetti; Roberta Franzini; Bruno Botta; Francesca Ghirga
Journal:  Molecules       Date:  2020-01-19       Impact factor: 4.411
  5 in total

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