Literature DB >> 21264408

Asymmetric synthesis of Pachastrissamine (Jaspine B) and its diastereomers via η3-allylpalladium intermediates.

Mikko Passiniemi1, Ari M P Koskinen.   

Abstract

A short route for the synthesis of Pachastrissamine (Jaspine B), an anhydrosphingosine derivative, and all three of its diastereomers is presented. The route consists of only 9 steps from the commercially available Garner's aldehyde. The furan framework is formed via an η(3)-allylpalladium intermediate.

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Year:  2011        PMID： 21264408     DOI： 10.1039/c0ob00643b

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  4 in total

Review 1.  Recently confirmed apoptosis-inducing lead compounds isolated from marine sponge of potential relevance in cancer treatment.

Authors:  Magbubah Essack; Vladimir B Bajic; John A C Archer
Journal:  Mar Drugs       Date:  2011-09-20       Impact factor: 6.085

Review 2.  Garner's aldehyde as a versatile intermediate in the synthesis of enantiopure natural products.

Authors:  Mikko Passiniemi; Ari Mp Koskinen
Journal:  Beilstein J Org Chem       Date:  2013-11-26       Impact factor: 2.883

3.  Synthesis and biological evaluation of carbocyclic analogues of pachastrissamine.

Authors:  Yongseok Kwon; Jayoung Song; Hoon Bae; Woo-Jung Kim; Joo-Youn Lee; Geun-Hee Han; Sang Kook Lee; Sanghee Kim
Journal:  Mar Drugs       Date:  2015-02-03       Impact factor: 5.118

4.  Stereodivergent synthesis of jaspine B and its isomers using a carbohydrate-derived alkoxyallene as C3-building block.

Authors:  Volker Martin Schmiedel; Stefano Stefani; Hans-Ulrich Reissig
Journal:  Beilstein J Org Chem       Date:  2013-11-19       Impact factor: 2.883
  4 in total

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