An efficient total synthesis of (+/-)-lycoramine.
[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.
Fan
Chun-An
CA
State Key Laboratory of Applied Organic Chemistry & Department of Chemistry, Lanzhou University, Lanzhou 730000, PR China.
Tu
Yong-Qiang
YQ
Song
Zhen-Lei
ZL
Zhang
En
E
Shi
Lei
L
Wang
Min
M
Wang
Baomin
B
Zhang
Shu-Yu
SY
D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry; D013237:Stereoisomerism
D047151:Amaryllidaceae Alkaloids; D020005:Propanols; C006463:allyl alcohol; C500482:lycoramine