Abstract
Opening and closing a chemical window: oxidation of the etheno-bridged [4.3.1]propelladienol 1 with pyridinium chlorochromate (PCC) affords oxa[5.6.5.6]fenestratetraene 2. The reduction of 2 with diisobutylaluminum hydride (DIBAl-H) leads to the regeneration of its precursor (1). These transformations most likely involve a [3,5]-sigmatropic rearrangement process.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Aza Compounds / chemistry*
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Bridged-Ring Compounds / chemistry*
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Cyclopropanes / chemistry*
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Diterpenes / chemistry
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Organometallic Compounds / chemistry
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Oxidation-Reduction
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Pyridinium Compounds / chemistry
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Quantum Theory
Substances
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Aza Compounds
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Bridged-Ring Compounds
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Cyclopropanes
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Diterpenes
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Organometallic Compounds
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Pyridinium Compounds
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aza(5.6.5.6)fenestratetrene
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oxa-(5.6.5.6)fenestratetrene
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salvileucalin B
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cyclopropane
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pyridinium chlorochromate
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diisobutylaluminum