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Pyranophane Transannular Diels—Alder Approach to (+)-Chatancin: A Biomimetic Asymmetric Total Synthesis.
- Source :
-
Journal of Organic Chemistry . 12/26/2003, Vol. 68 Issue 26, p9983-9987. 5p. 5 Diagrams. - Publication Year :
- 2003
-
Abstract
- An asymmetric total synthesis of (+)-chatancin was achieved via a transannular Diels-Alder (TADA) reaction of an in situ generated macrocyclic pyranophane pseudobase. The presented route constitutes the second of two proposed biosynthetic pathways that involves a TADA reaction. It links this diterpene biogenetically to the cembranoids. A set of TADA selection rules that rationalize the formation of (+)-chatancin from a dynamic equilibrium of four 2-hydroxy-2H-pyrane bicycles and their 16 potential TADA transition states are also outlined. Beyond the TADA reaction, highlights of the synthetic work include the assembly of a chiral acyclic macrocyclization substrate from (S)-citronellol and an efficient macrocyclization via a β-ketosulfoxyde/enone Michael addition. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 68
- Issue :
- 26
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 11963598
- Full Text :
- https://doi.org/10.1021/jo035193y