An efficient total synthesis of (+/-)-lycoramine.

Chun-An Fan, Yong-Qiang Tu, Zhen-Lei Song, En Zhang, Lei Shi, Min Wang, Baomin Wang, Shu-Yu Zhang

State Key Laboratory of Applied Organic Chemistry & Department of Chemistry, Lanzhou University, Lanzhou 730000, PR China.

Organic letters 2004 Dec 9

filter terms:

reaction: see text] A short and unique approach to (+/-)-lycoramine as one of the galanthamine-type alkaloids has been efficiently developed. The alternative advantage lies in that three stereocenters, including a crucial quaternary carbon center, were constructed with high diasteroselectivity via a key one-step NBS-mediated semipinacol rearrangement of the allylic alcohol.

Citation

Chun-An Fan, Yong-Qiang Tu, Zhen-Lei Song, En Zhang, Lei Shi, Min Wang, Baomin Wang, Shu-Yu Zhang. An efficient total synthesis of (+/-)-lycoramine. Organic letters. 2004 Dec 9;6(25):4691-4