A novel and highly stereoselective approach to aza-spirocycles. A short total synthesis of 2-epi-(+/-)-perhydrohistrionicotoxin and an unprecedented decarboxylation of 2-pyrones.
[reaction: see text] A novel and highly stereoselective synthesis of aza-spirocycles is described. An application of this methodology is illustrated as a short and concise total synthesis of 2-epi-(+/-)-perhydrohistrionicotoxin with high diastereomeric control at the aza-spirocenter. An unprecedented decarboxylation of the 2-pyrone ring is observed in this total synthesis effort.
McLaughlin
Michael J
MJ
Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
Hsung
Richard P
RP
Cole
Kevin P
KP
Hahn
Juliet M
JM
Wang
Jiashi
J
D000664:Amphibian Venoms / Q000138:chemical synthesis*; D001372:Aza Compounds / Q000138:chemical synthesis*; D002264:Carboxylic Acids / Q000737:chemistry*; D011753:Pyrones / Q000737:chemistry*; D013237:Stereoisomerism
D000664:Amphibian Venoms; D001372:Aza Compounds; D002264:Carboxylic Acids; D011753:Pyrones; C004792:perhydrohistrionicotoxin