A unified, RCM anchored approach to spiro[4.5]decane-based sesquiterpenoids: Collective synthesis of (±)-α & β-vetispirenes, (±)-β-vetivone, (±)-agarospirol and (±)-hinesol

[Display omitted] •A concise new approach to spiro[4.5]decane based sesquiterpenoids in which RCM reaction on a simple, stereoselectively crafted precursor furnishes a versatile intermediate (2,10-dimethylspiro[4.5]dec-1-en-6-one) has been delineated.•This platform intermediate has been elaborated t...

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Bibliographic Details
Published in:Tetrahedron letters 2019-06, Vol.60 (24), p.1570-1573
Main Authors: Athe, Sudhakar, Ghosh, Subhash, Mehta, Goverdhan
Format: Article
Language:English
Subjects:
RCM-reaction
Spiro[4.5]-dacane
Total synthesis
Vetivene sesquiterpenes
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Summary:[Display omitted] •A concise new approach to spiro[4.5]decane based sesquiterpenoids in which RCM reaction on a simple, stereoselectively crafted precursor furnishes a versatile intermediate (2,10-dimethylspiro[4.5]dec-1-en-6-one) has been delineated.•This platform intermediate has been elaborated to several spirocyclic sesquiterpenoid natural products namely α & β-vetispirenes, β-vetivone, agarospirol, hinesol, axenol and gleenol through short, efficient sequences.•The strategy developed here can find many more potential applications in the synthesis of spirocyclics. Collective syntheses of five spiro[4.5]decane framework bearing sesquiterpenoids, namely, α & β-vetispirenes, β-vetivone, agarospirol and hinesol as well as formal synthesis of axenol and gleenol from a readily available precursor cyclohexanone-β-ketoester via the intermediacy of a versatile intermediate (2,10-dimethylspiro[4.5]dec-1-en-6-one) have been accomplished in a concise manner.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.05.011