Chemoenzymatic approaches to the montanine alkaloids: a total synthesis of (+)-brunsvigine.
The readily available and enzymatically derived cis-1,2-dihydrocatechols 3a and 3b have been elaborated over 17 steps, including a novel radical addition/elimination sequence, into the enantiomer, (+)-1, of the montanine alkaloid brunsvigine [(-)-1].
Banwell
Martin G
MG
Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia. mgb@rsc.anu.edu.au
Kokas
Okanya J
OJ
Willis
Anthony C
AC
D000470:Alkaloids / Q000737:chemistry*; D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002396:Catechols / Q000737:chemistry; D007546:Isoquinolines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000470:Alkaloids; D047151:Amaryllidaceae Alkaloids; D002396:Catechols; D007546:Isoquinolines; C432323:brunsvigine; C517208:montanine