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Synlett 2018; 29(11): 1517-1519
DOI: 10.1055/s-0036-1592001
letter
© Georg Thieme Verlag Stuttgart · New York

A Biomimetic Synthesis of des-Hydroxy Paecilospirone

Zhen-Gao Feng
Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, USA   eMail: pettus@chem.ucsb.edu
,
G. Leslie Burnett
Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, USA   eMail: pettus@chem.ucsb.edu
,
Thomas R. R. Pettus*
Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, USA   eMail: pettus@chem.ucsb.edu
› InstitutsangabenT.R.R.P. is grateful for past financial support from the National Science Foundation (CHE-0806356) for this work.
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Publikationsverlauf

Received: 07. März 2018

Accepted: 02. April 2018

Publikationsdatum:
09. Mai 2018 (online)

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Dedicated to purveyors of truth: Tomáš Hudlický, Richard H. Schlessinger, Samuel J. Danishefsky

Abstract

The carbon framework of des-hydroxy paecilospirone was rapidly synthesized using a biomimetic approach whereby an enol ether and an ortho-quinone methide (o-QM), each derived from the same lactone, were combined to arrive at the complete carbon skeleton of paecilospirone.

Key words

ortho-quinone methide - Diels–Alder - paecilospirone - benzylic oxidation - enol ether

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1592001.
  • Supporting Information
 

  • References and Notes

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