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Total Synthesis of (−)‐Morphine
Author(s) -
Umihara Hirotatsu,
Yokoshima Satoshi,
Inoue Masayuki,
Fukuyama Tohru
Publication year - 2017
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/chem.201701438
Subject(s) - total synthesis , ring (chemistry) , morphine , transformation (genetics) , chemistry , stereochemistry , amine gas treating , singlet oxygen , oxygen , organic chemistry , biochemistry , pharmacology , gene , medicine
Asymmetric total synthesis of (−)‐morphine has been accomplished in 18 steps from commercially available 7‐methoxy‐2‐tetralone. Our synthesis features a simple transformation from a readily prepared chiral intermediate, construction of the E‐ring by acid‐mediated cyclization, and singlet oxygen‐mediated manipulation of the C‐ring. Transformation of the final stage involves construction of the morphinan skeleton by means of 1,6‐addition of in situ generated secondary amine.