Journal of Organic Chemistry p. 3989 - 3993 (1980)
Update date:2022-07-29
Topics:
Goldsmith, David J.
John, Thottathil K.
Kwong, Cecil D.
Painter, George R.
The preparation of three trichothecane-like compounds, olefin 9 and epoxides 10 and 23, is reported.Subjection of 9 to conditions of acid-catalyzed rearrangement followed by hydrogenation leads to (+/-)-aplysin.The anti epoxide 10 also undergoes rearrangement but with migration of the aryl group rather than the pyranyl oxygen to give 26.Syn epoxide 23 does not undergo skeletal rearrangement.Hydrogenation of olefin 9 affords (+/-)-filiformin.
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Doi:10.1007/BF00561344
(1980)Doi:10.1016/S0040-4039(00)71450-X
(1980)Doi:10.1016/0039-128X(80)90141-5
(1980)Doi:10.1021/ja01285a011
(1937)Doi:10.1021/ja01627a062
(1955)Doi:10.1021/jo01069a509
(1961)
