Literature DB >> 12889913

New strategy for the total synthesis of macrosphelides a and B based on ring-closing metathesis.

Yuji Matsuya1, Takanori Kawaguchi, Hideo Nemoto.   

Abstract

[reaction: see text] A new total synthesis of macrosphelides A and B using ring-closing metathesis (RCM) as a macrocyclization step is described. The substrate of the RCM could be synthesized from readily available chiral materials, methyl (S)-(+)-3-hydroxybutyrate and methyl (S)-(-)-lactate, with a high efficiency. The RCM proceeded in the presence of Grubbs' Ru-complex, providing a new effective synthetic route to these natural products.

Entities:  

Year:  2003        PMID: 12889913     DOI: 10.1021/ol0350689

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


  3 in total

1.  DFT investigation of the 1-octene metathesis reaction mechanism with the Phobcat precatalyst.

Authors:  Frans T I Marx; Johan H L Jordaan; Hermanus C M Vosloo
Journal:  J Mol Model       Date:  2009-05-31       Impact factor: 1.810

2.  Development of an advanced synthetic route to macrosphelides and its application to the discovery of a more potent macrosphelide derivative.

Authors:  Yu Mi Heo; Hunseok Lee; Young Kee Shin; Seung-Mann Paek
Journal:  Molecules       Date:  2014-09-29       Impact factor: 4.411

3.  Synthetic studies on bioactive natural polyketides: intramolecular nitrile oxide-olefin cycloaddition approach for construction of a macrolactone skeleton of macrosphelide B.

Authors:  Seung-Mann Paek; Young-Ger Suh
Journal:  Molecules       Date:  2011-06-10       Impact factor: 4.411

  3 in total

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