Approach to the Synthesis of Diterpenes with the Bicyclo[5.3.0]decane System: (±) 10- epi-tormesol

The synthesis of (±) 10- epi-tormesol, 27, has been achieved from (±) 1-acetyl-3a,6 dimethylhexahydroazulene 1, by coupling of 5, a dehydroderivative of 1, with 23. The same synthetic procedure afforded a series of diterpenes 24–26 and 28 with the same biannular system. Direct reduction of 1 with di...

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Bibliographic Details
Published in:Tetrahedron 1995-11, Vol.51 (45), p.12403-12416
Main Authors: S. Marcos, Isidro, M. Oliva, Isabel, Díez, David, Basabe, Pilar, M. Lithgow, Anna, F. Moro, Rosalina, M. Garrido, Narciso, G. Urones, Julio
Format: Article
Language:English
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Summary:The synthesis of (±) 10- epi-tormesol, 27, has been achieved from (±) 1-acetyl-3a,6 dimethylhexahydroazulene 1, by coupling of 5, a dehydroderivative of 1, with 23. The same synthetic procedure afforded a series of diterpenes 24–26 and 28 with the same biannular system. Direct reduction of 1 with different methods does not give the desired spatial relationship ( trans/cis) between Me-C 7/H-6/H-10 on the substrate, affording instead trans/trans (compounds 5 and 18) and cis/cis (compound 9). Indirect reduction: epoxydation followed by catalytic hydrogenation afforded the desired stereochemistry on the intermediate but deoxygenation caused epimerization at C-10. This synthetic achievement confirmed the original structure assigned to tormesol some years ago.
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(95)00796-B