Enantiodivergent synthesis of both enantiomers of marine alkaloids haliclorensin and isohaliclorensin, a constituent of halitulin.
Starting from (3R)-5-benzotriazolyl-3-phenylperhydropyrido[2,1-b][1,3]oxazole 9, the enantiodivergent syntheses of both enantiomers of the marine alkaloids haliclorensin 1 and isohaliclorensin 3 have been achieved. Our syntheses feature ring-expansion reactions for the formation of the aza-macrocycle ring system of 3 and sequential ring-expansion reactions (aza-Claisen rearrangement and Zip reaction) for the formation of the aza-macrocycle ring system of 1.
Zheng
Jian-Feng
JF
Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005, P R China.
Jin
Li-Ren
LR
Huang
Pei-Qiang
PQ
D000470:Alkaloids / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000470:Alkaloids; D000970:Antineoplastic Agents; D006573:Heterocyclic Compounds, 1-Ring; D006576:Heterocyclic Compounds, 4 or More Rings; C484766:haliclorensin; C484764:halitulin; C484765:isohaliclorensin