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A concise and enantioselective approach to the total synthesis of (−)-lasubine I |
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| Authors: | Shengyang Liu Xinxiang Peng Weiyi Hua Lixin Liao |
| Institution: | a Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, PR China b Xinjiang Technical Institute of Physical and Chemistry, Chinese Academy of Sciences, Urumuqi 830011, PR China c Department of Medicinal Chemistry, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, PR China d Department of Chemistry, University of New Mexico, Albuquerque, NM 87131-0001, USA e Shanghai Institute of Materia Medica, Shanghai Institutes of Biological Sciences, Chinese Academy of Sciences, Graduate School of the Chinese Academy of Sciences, Shanghai 201203, PR China |
| Abstract: | An efficient, enantioselective total synthesis of (−)-lasubine I (1) has been achieved in an overall 8.8% yield from readily available starting materials. The important features of this approach include the creation of stereogenic centers through two sequential highly stereoselective Roush allylborations and the use of SN2 cyclization and ring-closing metathesis reactions for the construction of the quinolizidine skeleton. |
| Keywords: | Lasubine Ring-closing metathesis Roush allylboration Quinolizidine |
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