Diels-Alder cycloaddition of o-quinonedimethides and alkylidene-5H-furan-2- ones: New and rapid access to lambertellol cores and arthrinone derivatives

Organic and Biomolecular Chemistry

Volumn 8, Issue 24, 2010, Pages 5490-5494

  Blanc, Romain ^a   Héran, Virginie ^a   Rahmani, Raphaël ^a   Commeiras, Laurent ^a   Parrain, Jean Luc ^a  

^a AIX MARSEILLE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY; POSITIVE IONS;

ALKYLIDENES; DIASTEREOSELECTIVE; DIELS-ALDER CYCLOADDITIONS; EFFICIENT SYNTHESIS;

CYCLOADDITION;

ALNUS;

EID: 78649503455     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0ob00448k     Document Type: Article

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49. 1H NMR spectrum of the crude product revealed the presence of a 1/0,9 mixture of the deshydrohalogenated and non-deshydrohalogenated naphtofurane respectively.
50. The stereochemistry was not assigned. For hetero Diels-Alder reactions with o-quinonedimethydes see ref. 16e.
51. Cycloaddition performed with lactone acetal, precursor of lactone aldehyde 2p led to the formation of the corresponding spiro-cycloadduct. Unfortunately, the acetal function was too sensitive and up to 40% of deprotected aldehyde 3p was recovered after purification on neutralized silica gel
52. The stereochemistry of the third diasteromer was not assigned.