123060-92-4Relevant academic research and scientific papers
Cationic cyclization of 2-alkenyl-1,3-dithiolanes: Diastereoselective synthesis of trans-decalins
Goncalves, Sylvie,Santoro, Stefano,Nicolas, Marc,Wagner, Alain,Maillos, Philippe,Himo, Fahmi,Baati, Rachid
, p. 3274 - 3285 (2011/06/25)
An unprecedented and highly diastereoselective 6-endo-trig cyclization of 2-alkenyl-1,3-dithiolanes has been developed yielding trans-decalins, an important scaffold present in numerous di- and triterpenes. The novelty of this 6-endo-trig cyclization stan
INFLUENCE OF METHOXY- AND METHYL-AROMATIC SUBSTITUENS ON STEREOCHEMISTRY OF THE PRODUCTS IN THE ACID-CATALIZED CYCLIZATION OF 2-(2-ARYLETHYL)-1,3,3-TRIMETHYLCYCLOHEXANOLS: STEREOCONTROLLED TOTAL SYNTHESIS OF (+/-)- NIMBIDIOL AND (+/-)-NIMBIOL
Banik, Bimal K.,Ghosh, Sukumar,Ghatak, Usha Ranjan
, p. 6947 - 6955 (2007/10/02)
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.
