Chemoenzymatic approaches to lycorine-type Amaryllidaceae alkaloids: total syntheses of ent-lycoricidine, 3-epi-ent-lycoricidine, and 4-deoxy-3-epi-ent-lycoricidine.
The readily available and enzymatically derived cis-1,2-dihydrocatechol 4 has been elaborated, over 11 steps including an Overman rearrangement, into the non-natural enantiomer, (-)-1, of the alkaloid lycoricidine [(+)-1]. Related chemistries have provided analogues 18, 19, and 26.
Matveenko
Maria
M
Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia.
Kokas
Okanya J
OJ
Banwell
Martin G
MG
Willis
Anthony C
AC
D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D004798:Enzymes / Q000737:chemistry*; D015394:Molecular Structure; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
C524025:4-deoxy-3-epi-ent-lycoricidine; D047151:Amaryllidaceae Alkaloids; D004798:Enzymes; D010617:Phenanthridines; C500283:lycoricidine