Literature DB >> 20586455

Synthesis of the guaianolide ring system via cycloaddition of a bicyclic carbonyl ylide with allyl propiolate.

Vaidotas Navickas1, Dmitry B Ushakov, Martin E Maier, Markus Ströbele, H-Jürgen Meyer.   

Abstract

A cyclic carbonyl ylide with a trans-annulated cyclopentane ring was generated by a Rh(2)(OAc)(4)-catalyzed reaction from a diazoketone precursor and trapped with allyl propiolate. The 1,3-dipolar cycloaddition led to the stereoselective formation of an oxygen-bridged polycycle. Via Curtius degradation, the cycloadduct was transformed to the ring skeleton typical of the sesquiterpene family of guaianolides.

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Year:  2010        PMID： 20586455     DOI： 10.1021/ol1012185

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


  4 in total

1.  Formal synthesis of (-)-englerin A and cytotoxicity studies of truncated englerins.

Authors:  Jing Xu; Eduardo J E Caro-Diaz; Ayse Batova; Steven D E Sullivan; Emmanuel A Theodorakis
Journal:  Chem Asian J       Date:  2012-03-13

2.  Hydrodealkenylative C(sp3)-C(sp2) bond fragmentation.

Authors:  Andrew J Smaligo; Manisha Swain; Jason C Quintana; Mikayla F Tan; Danielle A Kim; Ohyun Kwon
Journal:  Science       Date:  2019-05-17       Impact factor: 47.728

3.  A Double Allylation Strategy for Gram-Scale Guaianolide Production: Total Synthesis of (+)-Mikanokryptin.

Authors:  Xirui Hu; Silong Xu; Thomas J Maimone
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-03       Impact factor: 15.336

4.  Synthesis and Biological Evaluation of New (-)-Englerin Analogues.

Authors:  Laura López-Suárez; Lorena Riesgo; Fernando Bravo; Tanya T Ransom; John A Beutler; Antonio M Echavarren
Journal:  ChemMedChem       Date:  2016-03-23       Impact factor: 3.466
  4 in total

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