Literature DB >> 16119944

A Paterno-Büchi approach to the synthesis of merrilactone A.

Jone Iriondo-Alberdi1, Jesus E Perea-Buceta, Michael F Greaney.   

Abstract

A six-step approach to the tetracyclic core of merrilactone A is described that uses an intramolecular Paterno-Büchi photoaddition to install the key oxetane ring. Irradiation of bicyclic enone 16, constructed through cyclopentenone alkylation followed by a domino oxy-/carbopalladation reaction, produces the tetracyclic oxetane 17 in excellent yield, having the core carbon skeleton of the target compound merrilactone A. [reaction: see text]

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Year:  2005        PMID: 16119944     DOI: 10.1021/ol0514496

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


  7 in total

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2.  Stereodivergent synthesis of enantioenriched 4-hydroxy-2-cyclopentenones.

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Review 4.  Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis.

Authors:  Markus D Kärkäs; John A Porco; Corey R J Stephenson
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Review 5.  Application of Pauson-Khand reaction in the total synthesis of terpenes.

Authors:  Majid M Heravi; Leila Mohammadi
Journal:  RSC Adv       Date:  2021-11-29       Impact factor: 4.036

Review 6.  Oxetane synthesis through the Paternò-Büchi reaction.

Authors:  Maurizio D'Auria; Rocco Racioppi
Journal:  Molecules       Date:  2013-09-16       Impact factor: 4.411

Review 7.  Advances in the Phototriggered Synthesis of Single-Chain Polymer Nanoparticles.

Authors:  Ester Verde-Sesto; Agustín Blázquez-Martín; José A Pomposo
Journal:  Polymers (Basel)       Date:  2019-11-18       Impact factor: 4.329

  7 in total

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