Journal of Organic Chemistry p. 1904 - 1911 (1985)
Update date:2022-08-05
Topics:
Boger, Dale L.
Mullican, Michael D.
Hellberg, Mark R.
Patel, Mona
A preparation of optically pure, functionalized cis-Δ6-octalones starting with (-)-β-pinene (92percent ee) is detailed.The conversion of (-)-β-pinene to (-)-cis-nopinol (>97percent ee) and its utilization in the preparation of (4R,9R,10R)-(+)-4-(acetylamino)-9-(methoxycarbonyl)-cis-Δ6-1-octalone ethylene ketal (1), a cis-Δ6-1-octalone possessing the correct absolute configuration at three appropriately functionalized chiral centers characteristic of the morphine-related analgesics, is described.
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Doi:10.1002/jhet.5570220112
(1985)Doi:10.1021/jo00213a047
(1985)Doi:10.1021/acs.organomet.8b00474
(2018)Doi:10.1007/BF01131072
()Doi:10.1021/ja01495a026
(1960)Doi:10.1016/S0040-4039(00)89122-4
(1985)
