Stereoselective Synthesis of a Key Precursor of Halicholactone and Neohalicholactone
- 9 January 1998
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 63 (3) , 642-646
- https://doi.org/10.1021/jo971564x
Abstract
An efficient synthesis of a known precursor of halicholactone (1a) and neohalicholactone (1b) has been developed using the strategically functionalized key cyclopropane intermediate 2, which in turn has been synthesized via stereoselective cyclopropanation of trans-cinnamyl alcohol in the presence of the chiral dioxaborolane ligand 4. Elaboration of the above bifunctional cyclopropane to the target molecule was achieved in a relatively short reaction sequence and in good overall yield, representing a formal synthesis of the title compounds.Keywords
This publication has 4 references indexed in Scilit:
- Pteroenone: A Defensive Metabolite of the Abducted Antarctic Pteropod Clione antarcticaThe Journal of Organic Chemistry, 1995
- Structure and stereochemistry of constanolactones A-G, lactonized cyclopropyl oxylipins from the red marine alga Constantinea simplexThe Journal of Organic Chemistry, 1994
- High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoidsJournal of the American Chemical Society, 1991
- Isolation and structure of constanolactones A and B, new cyclopropyl hydroxy-eicosanoids from the temperate red alga constantinea simplexTetrahedron Letters, 1990