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Protecting group directed cyclization: asymmetric synthesis of both cis- and trans-dihydrexidine from a common precursor.
- Source :
-
Tetrahedron . Oct2013, Vol. 69 Issue 43, p8994-9000. 7p. - Publication Year :
- 2013
-
Abstract
- Abstract: 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. [Copyright &y& Elsevier]
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 69
- Issue :
- 43
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 90203646
- Full Text :
- https://doi.org/10.1016/j.tet.2013.08.042