Concise synthesis of two advanced intermediates for the asymmetric synthesis of polyhydroxylated indolizidine alkaloids |
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| Authors: | Xiao Zheng WenFang Zhu PeiQiang Huang |
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| Affiliation: | 1. Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China
2. Key Laboratory of Synthetic Chemistry of Natural Substances; Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China
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| Abstract: | A concise five-step approach to indolizidinones 10 and 11, two advanced intermediates for the asymmetric synthesis of polyhydroxylated indolizidine alkaloids, has been developed by using N-Cbz pyrrolidin-2-yl pyridin-2-yl sulfide 13 as the chiral building block. The method features a SmI2-mediated coupling of sulfide 13 with functionalized aldehyde 14 and a tandem N-deprotection-lactamization, which constitutes a stepwise “2 + 4” annulation method for the construction of the indolizidinone ring system of 12a. |
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