Concise and divergent total synthesis of swainsonine, 7-alkyl swainsonines, and 2,8a-diepilentiginosine via a chiral heterocyclic enaminoester intermediate

• Published in: Tetrahedron Vol. 64; no. 22; pp. 5005 - 5012
• Main Authors: Shi, Gao-Feng, Li, Jia-Qi, Jiang, Xiao-Ping, Cheng, Ying
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 26.05.2008; Elsevier
• Subjects: 2,8a-Diepilentiginosine; Chemistry; Chemistry, Organic; Heterocyclic enaminoester; Physical Sciences; Polyhydroxylated indolizidine; Science & Technology; Swainsonine; Total synthesis; Heterocyclic enaminoester; 2,8a-Diepilentiginosine; Polyhydroxylated indolizidine; Swainsonine; Total synthesis; ACID; ALPHA-MANNOSIDASE; INDOLIZIDINE; STEREOSELECTIVE TOTAL-SYNTHESIS; CASTANOSPERMINE; THERMAL-DECOMPOSITION; 2,8a-diepilentiginosine; swainsonine; DIACYL PEROXIDES; polyhydroxylated indolizidine; heterocyclic enaminoester; (+)-RETRONECINE; total synthesis; INHIBITOR; DRUG SWAINSONINE
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2008.03.080

The concise and divergent total syntheses of (−)-swainsonine, (−)-7-alkyl swainsonines, and (−)-2,8a-diepilentiginosine from a common chiral heterocyclic enaminoester intermediate in five-step sequences are presented. The highly efficient annulation reaction of the chiral heterocyclic enaminoester with various α,β-unsaturated carboxylates, and a straightforward carboxy inversion constituted the key features of the synthetic pathway. This work provides an example for divergent synthesis of different natural and unnatural polyhydroxylated indolizidines from a readily available platform. [Display omitted]