Literature DB >> 11485459

Resolution of an iridoid synthon, gastrolactol, by means of dynamic acetylation and lipase-catalyzed alcoholysis.

E M Santangelo1, D Rotticci, I Liblikas, T Norin, C R Unelius.   

Abstract

A short synthetic route to asymmetric iridoids was developed. The three key steps were an intramolecular [4 + 2] cycloaddition reaction of an enamine derivative of 8-oxocitral (2), a dynamic acetylation, and an enzymatic resolution of the gastrolactyl acetates 5a and 5b, iridoids with three stereocenters. Some regio- and stereoselective heterogeneous catalytic hydrogenations of double bonds in iridoid aglucones were discussed.

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Year:  2001        PMID: 11485459     DOI: 10.1021/jo015592y

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


  1 in total

1.  The absolute configuration of chrysomelidial: a widely distributed defensive component among oribotririid mites (Acari: Oribatida).

Authors:  Nobuhiro Shimizu; Ryota Yakumaru; Tomoyo Sakata; Satoshi Shimano; Yasumasa Kuwahara
Journal:  J Chem Ecol       Date:  2012-01-14       Impact factor: 2.626

  1 in total

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