A facile synthesis of 1,4-dideoxy-1,4-imino-l-ribitol (LRB) and (-)-8a-epi-swainsonine from d-glutamic acid

Article abstract of DOI:10.1016/j.tet.2011.04.075

A facile synthesis of (-)-8a-epi-swainsonine 2 and 1,4-dideoxy-1,4-imino-l- ribitol (LRB) 4 has been achieved by using the versatile building block 3, which was available from cheap d-glutamic acid. The new forming stereogenic center in synthesis of 2 was constructed by highly selective reduction of the ketone 13 with Li(t-BuO)₃AlH in THF (dr=95:5).