Enantioselective construction of substituted pyridine and a seven-membered carbocyclic skeleton: biomimetic synthesis of (−)-rupestine D, (−)-guaipyridine, (−)-epiguaipyridine, and (−)-cananodine and their stereoisomers. Issue 32 (5th August 2021)

• Record Type: Journal Article
• Authors: Zhang, Cun; Wang, Bianlin; Aibibula, Paruke; Zhao, Jiangyu; Aisa, Haji Akber
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 32(2021)
• Page Start: 7081
• Page End: 7084
• Publication Date: 2021-08-05
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob01299a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Guaipyridine alkaloids (−)-rupestine D, (−)-guaipyridine, (−)-epiguaipyridine, and (−)-cananodine together with two stereoisomers 8- epi -rupestine D and 5- epi -cananodine were synthesized enantioselectively from readily available citronellol. Abstract : Guaipyridine alkaloids (−)-rupestine D, (−)-guaipyridine, (−)-epiguaipyridine, and (−)-cananodine together with two stereoisomers 8- epi -rupestine D and 5- epi -cananodine were synthesized enantioselectively from readily available citronellol. The key steps in this synthesis are (i) intermolecular opening of a trisubstituted epoxide for the formation of a chiral center at C-8; (ii) ring-closing metathesis for the construction of a seven-membered carbocyclic ring; and (iii) biomimetic cyclization of a 1, 5-dicarbonyl compound for the construction of a pyridine-fused bicyclic skeleton.