- An efficient asymmetric synthesis of furofuran lignans: (+)-Sesamin and (-)-sesamin
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An efficient synthesis of (+)-sesamin 1a and (-)-sesamin 1b is described. The key reactions include highly stereoselective aldol condensation of piperonal 7 with the dianion of chiral oxazolidinone 8, followed by intramolecular ring cyclization of aldol product 11 in high yield.
- Kim, Ju-Cheun,Kim, Kwang-Hyun,Jung, Jae-Chul,Park, Oee-Sook
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- Synthesis of 2,6-Diaryl-4,8-dihydroxy-3,7-dioxabicyclooctanes
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A series of 2,6-diaryl-4,8-dihydroxy-3,7-dioxabicyclooctanes, including 4,8-dihydroxysesamin, a naturally occurring lignan, have been prepared via the corresponding dilactones.The 1H and 13C n.m.r. spectra have been compared and the bistoluene-p-sulphonate of 4,8-dihydroxyeudesmin has been reduced by lithium aluminium hydride to give (+/-)-eudesmin.Since this synthesis does not involve ring-opened intermediates and starts from a dilactone of established structure, it represents the first unequivocal synthesis of such a lignan.
- Pelter, Andrew,Ward, Robert S.,Watson, Derrick J.,Collins, Peter,Kay, I. Trevor
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p. 175 - 182
(2007/10/02)
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