A General Route toward the Synthesis of the Cladiellin Skeleton Utilizing a SmI2-Mediated Cyclization
- 4 January 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 71 (3) , 1172-1180
Abstract
An efficient synthesis of the cladiellin skeleton is reported utilizing methods that were previously developed in this laboratory. The approach is based on a SmI2-mediated cyclization reaction for the construction of the oxacyclononane unit. A [4 + 3] annulation strategy was used to create the octahydroisobenzofuran moiety. This route provides the cladiellin skeleton in only 14 steps without the use of protecting groups. The present approach also enabled the synthesis of the 3,7-diastereomer of the natural product polyanthellin A.Keywords
This publication has 27 references indexed in Scilit:
- Toward a General Route to the Eunicellin Diterpenes: The Asymmetric Total Synthesis of Deacetoxyalcyonin AcetateJournal of the American Chemical Society, 2004
- Enantioselective Total Synthesis of Briarellins E and F: The First Total Syntheses of Briarellin DiterpenesJournal of the American Chemical Society, 2003
- Selective hydroboration of alkenes and alkynes in the presence of aldehydes and ketonesCanadian Journal of Chemistry, 1998
- Synthesis of (.+-.)-4-De(3-hydroxypropionyl)betaenone B, an advanced model for the betaenones and stamphyloxin IThe Journal of Organic Chemistry, 1988
- Redox chemistry of hydrogen peroxide in anhydrous acetonitrileInorganic Chemistry, 1986
- Reaction of [14]annulene with tricarbonyltriamminechromium(0). Synthesis and structure of hexacarbonyl-trans-6a,12a-dihydrooctalenedichromium(0)Journal of the American Chemical Society, 1971
- Synthetic applications of N-carboalkoxysulfamate estersJournal of the American Chemical Society, 1970
- Mechanism of photoisomerization of cyclohexenones. 10-Hydroxymethyl-.DELTA.1,9-2-octalone. Question of hydrogen abstraction from benzene by ketone tripletsJournal of the American Chemical Society, 1970
- Mechanism of the Wolff rearrangement. IIJournal of the American Chemical Society, 1970
- Bromohydrins from Olefins and N-Bromosuccinimide in WaterJournal of the American Chemical Society, 1955