Pedrolane, a Polycyclic Diterpene Scaffold Containing a Bicyclo[2.2.1]heptane System, from Euphorbia pedroi

Ricardo J. Ferreira, Gabriella Spengler, Andreas Orthaber, Daniel J.V.A. Dos Santos, Maria José U. Ferreira

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

Pedrolide (1), a diterpenoid with an unprecedented carbon skeleton, pedrolane, containing a bicycle[2.2.1]heptane system, is reported. This structural feature is hypothesized to involve an intramolecular cyclization, via Michael addition, and a ring contraction, via 1,2-alkyl shift or a Pinacol rearrangement of rings A and B, from a tigliane-type 5/7/6/3-tetracyclic ring precursor. The structure of 1 was established using spectroscopic techniques, single-crystal X-ray diffraction, and ab initio calculations. Pedrolide reversed multidrug resistance mediated by P-glycoprotein.

Original languageEnglish
Pages (from-to)274-278
Number of pages5
JournalOrganic Letters
Volume23
Issue number2
DOIs
Publication statusPublished - 15 Jan 2021
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2020 American Chemical Society.

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