Journal
ORGANIC LETTERS
Volume 23, Issue 2, Pages 274-278Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c03647
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Funding
- European Structural & Investment Funds through the COMPETE Programme
- FCT, Portugal (Fundacao para a Ciencia e a Tecnologia) [SAICTPAC/0019/2015, PTDC/MED-QUI/30591/2017]
- Swedish Research Council (Vetenskapsradet) [2017-03727]
- FCT [SFRH/BD/84285/2012]
- [GINOP-2.3.2-15-2016-00012]
- Fundação para a Ciência e a Tecnologia [SAICTPAC/0019/2015, PTDC/MED-QUI/30591/2017] Funding Source: FCT
- Swedish Research Council [2017-03727] Funding Source: Swedish Research Council
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Pedrolide is a diterpenoid with a unique carbon skeleton, pedrolane, which can reverse multidrug resistance mediated by P-glycoprotein.
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.
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