1.
J Am Chem Soc
; 142(26): 11376-11381, 2020 07 01.
Article
in English
| MEDLINE
| ID: mdl-32573211
ABSTRACT
We report a concise, stereocontrolled synthesis of the neurotoxic sesquiterpenoid (-)-picrotoxinin (1, PXN). The brevity of the route is due to regio- and stereoselective formation of the [4.3.0] bicyclic core by incorporation of a symmetrizing geminal dimethyl group at C5. Dimethylation then enables selective C-O bond formation in multiple intermediates. A series of strong bond (C-C and C-H) cleavages convert the C5 gem-dimethyl group to the C15 lactone of PXN.
Subject(s)
Picrotoxin/analogs & derivatives , Molecular Conformation , Picrotoxin/chemical synthesis , Picrotoxin/chemistry , Sesterterpenes , Stereoisomerism
2.
J Pharm Sci
; 72(10): 1131-4, 1983 Oct.
Article
in English
| MEDLINE
| ID: mdl-6139469
ABSTRACT
Preparation of some simple lactone analogues of picrotoxin and their biological evaluation is reported. Certain analogues possessed activity, but at potencies insufficient to warrant further work.