Literature DB >> 11678694

A new total synthesis of the marine tunicate alkaloid lepadiformine.

P Sun1, C Sun, S M Weinreb.   

Abstract

[reaction: see text]. A total synthesis of racemic lepadiformine has been achieved via a route that utilizes as key steps a novel stereocontrolled intramolecular spirocyclization of an allylsilane/N-acyliminium ion and the application of our radical-based methodology for production of N-acylimines from o-aminobenzamides.

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Year:  2001        PMID: 11678694     DOI: 10.1021/ol010179y

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


  5 in total

Review 1.  Studies on total synthesis of the cylindricine/fasicularin/lepadiformine family of tricyclic marine alkaloids.

Authors:  Steven M Weinreb
Journal:  Chem Rev       Date:  2006-06       Impact factor: 60.622

2.  Total synthesis of lepadiformine alkaloids using N-Boc α-amino nitriles as trianion synthons.

Authors:  Matthew A Perry; Matthew D Morin; Brian W Slafer; Scott D Rychnovsky
Journal:  J Org Chem       Date:  2012-03-13       Impact factor: 4.354

3.  Aza-[3 + 3] Annulations: A New Unified Strategy in Alkaloid Synthesis.

Authors:  Grant S Buchanan; John B Feltenberger; Richard P Hsung
Journal:  Curr Org Synth       Date:  2010-08-01       Impact factor: 1.975

4.  Enantioselective Aza-Sakurai Cyclizations: Dual Role of Thiourea as H-Bond Donor and Lewis Base.

Authors:  Yongho Park; Corinna S Schindler; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2016-11-03       Impact factor: 15.419

5.  Total Synthesis of (-)-Voacinol and (-)-Voacandimine C.

Authors:  Kristen M Flynn; In-Soo Myeong; Taylor Pinto; Mohammad Movassaghi
Journal:  J Am Chem Soc       Date:  2022-05-11       Impact factor: 16.383

  5 in total

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