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Total Syntheses of Resin Glycosides Murucoidins IV and V

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journal contribution
posted on 22.06.2019, 20:29 by Jing Fang, Jing Zeng, Jiuchang Sun, Shuxin Zhang, Xiong Xiao, Zimin Lu, Lingkui Meng, Qian Wan
Murucoidins IV and V, two bioactive resin glycosides with complex yet similar structures isolated from the morning glory family, were synthesized in a convergent manner. All of the glycosylations in these syntheses including the key [3 + 2] coupling were achieved by our recently developed interrupted Pummerer reaction mediated (IPRm) glycosylations. The broad functional group compatibility of IPRm glycosylation allowed us to employ a latent-active concept and a single-pot transient protection–glycosylation–deprotection strategy which significantly improved the global synthetic efficiency.