Journal of the Chemical Society. Perkin transactions I p. 793 - 802 (1996)
Update date:2022-08-04
Topics:
Yuasa, Yoko
Ando, Jun
Shibuya, Shiroshi
Cyclisation of the O-stannyl ketyl, generated from the aldehyde 17 by reaction with tributyltin hydride in the presence of AIBN, gives the 5-benzyloxymethyl-7-hydroxypyrrolooxazolidin-2-ones as a diastereoisomeric mixture of 7α-ol 18 and 7β-ol 19 (2:1), with high diastereoselectivity with respect to the 5,7a positions. (+)-Bulgecinine 8 is enantioselectively synthesised by stereospecific reduction of the ketone 20, derived from compounds 18 and 19. In a similar way, cyclisation of compound 40 gives a 2:1 mixture of compounds 41 and 42. Conversion of compound 41 into (-)-desoxoprosopinine 9 is successfully achieved.
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Doi:10.1021/ic951627z
(1996)Doi:10.1007/BF00851192
()Doi:10.1021/acs.orglett.7b01886
(2017)Doi:10.1039/c2ob25691f
(2012)Doi:10.1016/0957-4166(96)00101-2
(1996)Doi:10.1016/0957-4166(96)00150-4
(1996)
