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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
› Author AffiliationsT.R.R.P. is grateful for past financial support from the National Science Foundation (CHE-0806356) for this work.
Further Information

Publication History

Received: 07 March 2018

Accepted: 02 April 2018

Publication Date:
09 May 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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  • 15 Compound 5: 1H NMR (500 MHz, CDCl3) δ = 7.30–7.24 (m, 2 H), 7.16 (t, J = 7.9 Hz, 1 H), 6.95–6.90 (m, 2 H), 6.80 (d, J = 7.9 Hz, 1 H), 5.30 (s, 1 H), 5.25 (d, J = 12.8 Hz, 1 H), 5.07 (d, J = 12.8 Hz, 1 H), 3.30 (dd, J = 17.6, 5.5 Hz, 1 H), 3.01–2.84 (m, 3 H), 2.36–2.25 (m, 1 H), 1.77–1.67 (m, 2 H), 1.46–1.07 (m, 22 H), 0.87 (t, J = 7.0 Hz, 3 H), 0.83 (t, J = 7.1 Hz, 3 H). 13C NMR (126 MHz, CDCl3) δ = 204.8, 153.5, 150.0, 141.0, 138.2, 129.8, 126.9, 126.7, 122.4, 121.4, 120.6, 115.7, 114.5, 111.6, 70.6, 41.9, 38.2, 31.8, 31.8, 30.6, 29.6, 29.4, 29.4, 29.2, 29.1, 26.8, 26.1, 24.6, 22.7, 22.6, 14.1, 14.1. IR νmax (neat): 3393, 2925, 2854, 1670, 1607, 1455, 1287, 1258, 927. HRMS (ESI+) calcd for C32H44O4Na [M+Na]+: 515.3137; found: 515.3126