Literature DB >> 20420396

Total syntheses of (+)-fawcettimine and (+)-lycoposerramine-B.

Yasunari Otsuka1, Fuyuhiko Inagaki, Chisato Mukai.   

Abstract

The total synthesis of (+)-fawcettimine was completed in a highly stereoselective manner starting from the oxatricyclo[7.3.0.0(1,5)]dodecanedione derivative. The crucial step in this total synthesis involves the efficient construction of the azonane framework by the intramolecular Mitsunobu reaction. Furthermore, the first total synthesis of (+)-lycoposerramine-B was also accomplished via the common synthetic intermediate.

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Year:  2010        PMID: 20420396     DOI: 10.1021/jo100499h

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


  4 in total

1.  Total synthesis of (+)-sieboldine a: evolution of a pinacol-terminated cyclization strategy.

Authors:  Stephen M Canham; David J France; Larry E Overman
Journal:  J Org Chem       Date:  2012-06-26       Impact factor: 4.354

2.  Total synthesis of the Lycopodium alkaloid serratezomine A using free radical-mediated vinyl amination to prepare a β-stannyl enamine linchpin.

Authors:  Julie A Pigza; Jeong-Seok Han; Aroop Chandra; Daniel Mutnick; Maren Pink; Jeffrey N Johnston
Journal:  J Org Chem       Date:  2012-12-28       Impact factor: 4.354

3.  Unified total syntheses of fawcettimine class alkaloids: fawcettimine, fawcettidine, lycoflexine, and lycoposerramine B.

Authors:  Guojun Pan; Robert M Williams
Journal:  J Org Chem       Date:  2012-05-07       Impact factor: 4.354

4.  Synthesis of cis-hydrindan-2,4-diones bearing an all-carbon quaternary center by a Danheiser annulation.

Authors:  Gisela V Saborit; Carlos Cativiela; Ana I Jiménez; Josep Bonjoch; Ben Bradshaw
Journal:  Beilstein J Org Chem       Date:  2018-10-09       Impact factor: 2.883

  4 in total

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