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• W1806222568 abstract "Formal total synthesis of ent-codeinone and ent-codeine was accomplished via the total synthesis of ent-neopinone attained in 14 steps from β-bromoethylbenzene. The key steps included (i) enzymatic dihydroxylation of β-bromoethylbenzene with E. coli JM109 (pDTG601a), an organism that overexpresses toluene dioxygenase, (ii) a Heck reaction to establish C-13 stereogenic center, (iii) aldol condensation, and (iv) 1,6-conjugate addition of the ethylamino side chain to C-9. Several other modes of construction of the C-9 and C-14 centers were also investigated: Mannich cyclization, and aza-Prins reaction. The synthesis of ent-codeinone was formalized by intersecting Fukuyama’s recently published approach. Experimental and spectral data are provided for all new compounds." @default.
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• W1806222568 date "2011-06-01" @default.
• W1806222568 modified "2023-10-16" @default.
• W1806222568 title "Chemoenzymatic total synthesis of<i>ent</i>-neopinone and formal total synthesis of<i>ent</i>-codeinone from β-bromoethylbenzene*" @default.
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• W1806222568 doi "https://doi.org/10.1139/v11-071" @default.
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