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Synfacts 2025; 21(01): 6
DOI: 10.1055/a-2467-5582
DOI: 10.1055/a-2467-5582
Synthesis of Natural Products
Formal Synthesis of (±)-Morphine
Kage M,
Yamakoshi H,
Tabata M,
Ohashi E,
Noguchi K,
Watanabe T,
Uchida M,
Takada M,
Ikeuchi K,
Nakamura S.
*
Nagoya City University, Japan
Oxidative Generation of Isobenzofurans from Phthalans: Application to the Formal Synthesis of (±)-Morphine.
Chem. Sci. 2024;
15: 19070-19076
DOI: 10.1039/d4sc05890a
Oxidative Generation of Isobenzofurans from Phthalans: Application to the Formal Synthesis of (±)-Morphine.
Chem. Sci. 2024;
15: 19070-19076
DOI: 10.1039/d4sc05890a
Keywords
(±)-morphine - alkaloid natural products - Heck reaction - Henry reaction - oxidative furan Diels–Alder reaction
Significance
Nakamura and co-workers report the formal synthesis of morphine via an oxidative Diels–Alder reaction. The synthesis showcases a novel method of accessing isobenzofurans from phthalans.
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Comment
Henry reaction of C, followed by elimination, affords key-step precursor E. Subjecting E to oxidative conditions at high temperature affords G en route to J and morphine.
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Publication History
Article published online:
20 December 2024
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