1456722-35-2Relevant academic research and scientific papers
Protecting group directed cyclization: Asymmetric synthesis of both cis- and trans-dihydrexidine from a common precursor
Malhotra, Rajesh,Chakrabarti, Sagar,Dey, Tushar K.,Dutta, Swarup,Alapati, Krishna Babu,Dutta, Shantanu,Roy, Subho,Basu, Sourav,Hajra, Saumen
, p. 8994 - 9000 (2013)
Protection group of amino- and tethered o-arene functionality of 1,4-aryl-2-amino-1-butanol derived from l-serine dictates the cyclization mode under acidic conditions leading to reverse diastereoselectivity. N-Boc and acetal protected amino alcohol undergo cascade cyclization providing exclusively cis-dihydrexidine via reduction, where formation of C-ring (isoquinoline unit) prior to Friedel-Crafts cyclization control the cis-stereochemistry of the B-ring. N-Cbz and O-benzyl protection direct first F-C cyclization yielding the trans-1-aryl-2-aminotetralin and subsequent deprotection-cyclization forming the C-ring afforded dihydrexidine.
