1.
Ernst Schering Res Found Workshop
; (32): 103-48, 2000.
Article
in English
| MEDLINE
| ID: mdl-11077607
Subject(s)
Biological Products/chemical synthesis , Biological Products/pharmacology , Hydrocarbons, Cyclic , Imines , Animals , Biological Products/chemistry , Dinoflagellida/chemistry , Epoxy Compounds/chemical synthesis , Epoxy Compounds/chemistry , Heterocyclic Compounds, 3-Ring/chemical synthesis , Heterocyclic Compounds, 3-Ring/chemistry , Macrolides , Marine Biology , Marine Toxins/chemical synthesis , Marine Toxins/chemistry , Methods , Porifera/chemistry , Sesquiterpenes/chemical synthesis , Sesquiterpenes/chemistry , Thiazoles/chemical synthesis , Thiazoles/chemistry
2.
Org Lett
; 2(6): 763-6, 2000 Mar 23.
Article
in English
| MEDLINE
| ID: mdl-10754678
ABSTRACT
[formula: see text] (-)-Gymnodimine is a member of a unique class of potent marine toxins possessing imines within a spirocylic array. Herein we report the synthesis of the tetrahydrofuran fragment and a strategy toward the spirocyclic imine fragment of this family of toxins. Key reactions include an asymmetric anti-aldol reaction to set the stereochemistry of the tetrahydrofuran and a formal, intermolecular Diels-Alder reaction involving an alpha-methylene-delta-lactam and a dienyne.