Efficient total synthesis of (-)-ilimaquinone

Journal of Organic Chemistry

Volumn 63, Issue 17, 1998, Pages 5890-5894

  Poigny, Stéphane ^a   Guyot, Michèle ^a   Samedi, Mohammad ^a  

^a MUSÉUM NATIONAL D'HISTOIRE NATURELLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ILIMAQUINONE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; HYDROGENATION; PROTON NUCLEAR MAGNETIC RESONANCE; SPONGE (PORIFERA); STEREOCHEMISTRY; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 0032555406     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9805192     Document Type: Article

References (32)

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25. 2 provided 19 and 20 in a ratio of 4:1, and in addition, the reduction of exo-olefin having a 1,4-dimethoxybenzene side chain over Pd/C furnished a mixture of β/α in a ratio of 3:2 (see ref 13), which is the result of steric hindrence as reported. We reasoned that in addition of steric effects due to drimane skeleton, the tetramethoxybenzene moiety could have an interaction with the catalyst surface during the reduction of olefin 18 over Pd/C favoring the β-isomer 19 as a major product.
26. 2) to provide a methylated product that was identical in all respects (TLC, NMR, IR) with compound 23.
27. 4 (few drops) led to the total destruction of starting material within a few minutes.
28. 4 (few drops) led to the total destruction of starting material within a few minutes.
29. The pH of the reaction measured in the beginning as we have mentioned was 1.3, and at the end of reaction, it dropped to ∼0.7.
30. Manuscript in preparation.
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