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The Enantioselective Total Synthesis of (−)‐Myltaylenol
Author(s) -
Doye Sven,
Hotopp Torsten,
Wartchow Rudolf,
Winterfeldt Ekkehard
Publication year - 1998
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(19980807)4:8<1480::aid-chem1480>3.0.co;2-6
Subject(s) - enantioselective synthesis , chemistry , organic chemistry , catalysis
The unusual sesquiterpenoid alcohol (−)‐myltaylenol , which bears three consecutive quartenary carbon atoms, is synthesized in an overall yield of 6.5 % (below). The key step of the synthesis is a stereoselective intramolecular Diels–Alder reaction of a vinyl sulfonic ester followed by a novel oxidative ring cleavage employing molecular oxygen and giving rise to a hydroxyketone directly.