Synthesis of (−)-Morphine
- 28 September 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (42) , 12416-12417
- https://doi.org/10.1021/ja027882h
Abstract
The preparation of the diastereomerically pure β-tetralone ketal 4 is reported. Intramolecular alkylidene C−H insertion followed by hydrolysis of 4 proceeded to give the enantiomerically pure cyclopentene 15. The key step in this synthesis was the bis-intramolecular cyclization of keto aldehyde 2 to give the tetracyclic intermediate 20. Enone 20 was converted over several steps to (−)-morphine 1.Keywords
This publication has 14 references indexed in Scilit:
- Efficient Intramolecular C-H Insertion by an Alkylidene Carbene Generated from a Vinyl ChlorideThe Journal of Organic Chemistry, 1995
- Morphine: New aspects in the study of an ancient compoundLife Sciences, 1994
- Asymmetric synthesis of either enantiomer of opium alkaloids and morphinans. Total synthesis of (-)- and (+)-dihydrocodeinone and (-)- and (+)-morphineJournal of the American Chemical Society, 1993
- Quaternary ammonium tetrakis(diperoxotungsto)phosphates(3-) as a new class of catalysts for efficient alkene epoxidation with hydrogen peroxideThe Journal of Organic Chemistry, 1988
- Facile syntheses of potent dopaminergic agonists and their effects on neurotransmitter releaseJournal of Medicinal Chemistry, 1978
- A rapid, high-yield conversion of codeine to morphineJournal of Medicinal Chemistry, 1977
- Studies in the (+)-Morphinan Series I. An Alternative Conversion of (+)-Dihydrocodeinone into (+)-CodeineHETEROCYCLES, 1977
- Synthesis and pharmacology of some 2-aminotetralins. Dopamine receptor agonistsJournal of Medicinal Chemistry, 1975
- Reductive cleavage of sulfonamides with sodium bis(2-methoxyethoxy)aluminum hydrideThe Journal of Organic Chemistry, 1972
- IV.—Etherification of derivatives of β-naphtholJournal of the Chemical Society, Transactions, 1900