Tetrahedron p. 6947 - 6955 (1988)
Update date:2022-07-29
Topics: Total synthesis Cyclization Acid-Catalyzed Stereocontrolled Sterechemistry Methoxy-aromatic Methyl-aromatic 2-(2-arylethyl)-1,3,3-trimethylcyclohexanols Nimbidiol Nimbol
Banik, Bimal K.
Ghosh, Sukumar
Ghatak, Usha Ranjan
The distributions of the trans- and the cis-podocarpatrienes (5c-g) and (6c-g) in the cyclialkylation reaction of the easily accesible 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 synthesis of the modified diterpenes (+/-)-nimbidiol (7) and (+/-)-nimbiolmethylether (18) have been realized.
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Doi:10.1021/j100313a049
(1988)Doi:10.1039/b801909f
(2008)Doi:10.1021/ol800946x
(2008)Doi:10.1039/C8CC07470D
(2018)Doi:10.1021/om00140a031
(1986)Doi:10.1248/cpb.34.603
(1986)