TY - JOUR
T1 - Approaches to the synthesis of the galbulimima alkaloid himandrine
AU - O'Connor, Patrick D.
AU - Del Signore, Giuseppe
AU - McLachlan, Matthew M.W.
AU - Willis, Anthony C.
AU - Mander, Lewis N.
PY - 2010
Y1 - 2010
N2 - The hexacyclic skeleton of himandrine (2), which is present in 15 of the more complex alkaloids obtained from the bark of the tropical rain forest tree Galbulimima belgraveana has been prepared by means of a 19-step synthesis beginning with the known [3.2.1]-benzobicyclooctene intermediate 9. An alternative approach is also described, thus far culminating in 34. Key transformations include DielsAlder cycloadditions, ring contractions, a Curtius rearrangement, a Birch reduction, an intramolecular nucleophilic amination, and a palladium-mediated alkene amination.
AB - The hexacyclic skeleton of himandrine (2), which is present in 15 of the more complex alkaloids obtained from the bark of the tropical rain forest tree Galbulimima belgraveana has been prepared by means of a 19-step synthesis beginning with the known [3.2.1]-benzobicyclooctene intermediate 9. An alternative approach is also described, thus far culminating in 34. Key transformations include DielsAlder cycloadditions, ring contractions, a Curtius rearrangement, a Birch reduction, an intramolecular nucleophilic amination, and a palladium-mediated alkene amination.
UR - http://www.scopus.com/inward/record.url?scp=77957722848&partnerID=8YFLogxK
U2 - 10.1071/CH10252
DO - 10.1071/CH10252
M3 - Article
SN - 0004-9425
VL - 63
SP - 1477
EP - 1491
JO - Australian Journal of Chemistry
JF - Australian Journal of Chemistry
IS - 10
ER -