Abstract
The distributions of the trans-and the cis-podocarpatrienes (5c-g) and (6c-g) in the cyclialkylation reaction of the easily accessible cyclohexanols (4c-g) under a mild condition have been investigated. The cyclohexanol precursors having unactivated aromatic ring proceeds with high stereoselectivity leading to the respective trans-products, while the substrates with an electron donating methoxy or a methyl substituent with respect to the site of electrophilic attack result in the corresponding cis-and the trans-product mixtures. Consistent mechanisms for these stereochemical results have been advanced. Based on these results simple syntheses of the modified diterpenes (±)-nimbidiol (7) and (±)-nimbiolmethylether (18) have been realized.
Original language | English |
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Pages (from-to) | 6947-6955 |
Number of pages | 9 |
Journal | Tetrahedron |
Volume | 44 |
Issue number | 22 |
DOIs | |
State | Published - 1988 |
Externally published | Yes |