A Cascade Strategy Enables a Total Synthesis of (±)‐Morphine | Zendy

Chu Shuyu | Zendy; Münster Niels | Zendy; Balan Tudor | Zendy; Smith Martin D. | Zendy

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A Cascade Strategy Enables a Total Synthesis of (±)‐Morphine

Author(s) -

Chu Shuyu,

Münster Niels,

Balan Tudor,

Smith Martin D.

Publication year - 2016

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201608526

Subject(s) - total synthesis , morphine , chemistry , benzofuran , stereochemistry , stereoselectivity , metathesis , salt metathesis reaction , combinatorial chemistry , organic chemistry , catalysis , pharmacology , polymer , polymerization , medicine

Morphine has been a target for synthetic chemists since Robinson proposed its correct structure in 1925, resulting in a large number of total syntheses of morphine alkaloids. Here we report a total synthesis of (±)‐morphine that employs two key strategic cyclizations: 1) a diastereoselective light‐mediated cyclization of an O‐arylated butyrolactone to form a tricyclic cis‐fused benzofuran and 2) a cascade ene–yne–ene ring closing metathesis to forge the tetracyclic morphine core. This approach enables a short and stereoselective synthesis of morphine in an overall yield of 6.6 %.

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