Synthetic studies of ingenol: Synthesis of in,out- tricyclo[7.4.1.01,5]tetradecan-14-one

Tetrahedron Letters

Volumn 41, Issue 20, 2000, Pages 3927-3930

  Kigoshi, Hideo ^a   Suzuki, Yuto ^a   Aoki, Kenta ^a   Uemura, Daisuke ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

INGENOL;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGENATION; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 0034697496     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00519-0     Document Type: Article

References (30)

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22. The global minima were calculated in a Multiconformer conformational search using MacroModel (Version 6.0).
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26. Compound 9 was obtained as a mixture of α- and γ-allylic chlorides, which was employed for the next step without separation.
27. 2/THF, t-BuOK-KI/t-BuOH, and t-BuOK, 18-crown-6/t-BuOH, none of them were found to be more effective.
28. 4 in EtOH to give alcohol 15 (39%) and its diastereomeric alcohol (37%). Alcohol 15 exhibited an NOE between the oxymethine proton and the allylic proton, suggesting that the oxymethine group and the vinyl group in 15 are on the opposite side of the cyclopentane ring to each other. This finding indicates that the carbonyl group and the vinyl group in 10b are on the opposite side of the cyclopentane ring to each other and thus 10a possesses the desired stereochemistry for the synthesis of 2.
29. +, 100), 188 (21).
30. +) 206.1671, found 206.1643.