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Stereoselective Synthesis of the Quettamine Skeleton 1)
Author(s) -
Dirnberger Doris,
Wiegrebe Wolfgang
Publication year - 1990
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19903230603
Subject(s) - diastereomer , chemistry , ketone , stereoselectivity , stereochemistry , skeleton (computer programming) , ring (chemistry) , closure (psychology) , derivative (finance) , dithiane , catalysis , organic chemistry , economics , computer science , financial economics , market economy , programming language
A synthesis of the quettamine skeleton 29 is described comprising ring closure of the diastereomeric phenolic 1‐(α‐bromobenzyl)‐tetrahydroisoquinolines 27a and 27b . In both cases only one diastereomer was obtained. NOE‐experiments confirm Shamma's 23) assignments concerning the stereochemistry. ‐ Various attemps to cleave the dithiane derivative 5 of an α‐amino ketone in order to obtain the ketone 6 failed on account of the non‐bonding electron pair at the N‐atom.