17132-48-8Relevant articles and documents
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Adams,Van Duuren
, p. 5349 (1952)
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Absolute configuration and synthesis of β- and δ-lactones present in the pheromone system of the giant white butterfly Idea leuconoe
Stritzke, Katja,Schulz, Stefan,Nishida, Ritsuo
, p. 3884 - 3892 (2007/10/03)
Males of the giant white butterfly Idea leuconoe release a complex mixture of compounds during courtship. Besides alkaloids, aromatics, terpenoids and hydrocarbons, several lactones have been identified in the pheromone bouquet. Two simple stereoselective methods to create the lactones in good enantiomeric excesses have been developed. The generation of the stereocenters of the β-lactones la and lb is based on a controlled C-C coupling by a Horner-Wadsworth-Emmons approach, followed by asymmetric dihydroxylation, whereas the synthesis of the δ-lactone 3b uses an enantioselective hydrogenation of a dioxoalkanoate precursor. The absolute configurations of the natural lactones 1a, 1b and 3b were determined by gas chromatography on a chiral stationary phase. Both 1a and 1b are of (S,S) configuration, suggesting their biosynthetic origin from (-)-viridifloric acid (7a) or (-)norviridifloric acid (7b), respectively. In contrast, natural 3b is a mixture of all enantiomers, in which the (5S,7S) enantiomer dominates. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
Pyrrolizidine Alkaloid Analogues. Synthesis of 11-Membered Macrocyclic Diesters of (+)-Heliotridine
Hagan, Desmond B.,Robins, David J.
, p. 1165 - 1168 (2007/10/02)
The first synthesis of macrocyclic diesters incorporating (+)-heliotridine has been achieved.Treatment of (+)-heliotridine (1) with different glutaric anhydride derivatives produced mainly the corresponding 9-monoesters of heliotridine.Lactonisation was carried out after formation of the pyridine-2-thiol esters to give a range of 11-membered macrocyclic diesters of heliotridine.The structures of these new pyrrolizidine alkaloid analogues were established by comparison of their (1)H n.m.r. and mass spectra with those of natural macrocyclic pyrrolizidine alkaloids.Attempts to make 10-membered macrocyclic diesters of heliotridine were unsuccessful.
