A general approach to the stereoselective synthesis of spiroketals. A total synthesis of the pheromones of the olive fruit fly and related compounds
A general, highly stereoselective approach to the synthesis of spiroketal systems of the 1,7-dioxaspiro[5.5]undecane and 1,6-dioxaspiro[4.5]decane families is discussed. The key reaction in the approach features oxidation of a suitably substituted furfurol derivative 1 to afford pyranone 2, which su...
Saved in:
Published in | Journal of the American Chemical Society Vol. 110; no. 6; pp. 1901 - 1910 |
---|---|
Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
01.03.1988
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
Cover
Loading…
Summary: | A general, highly stereoselective approach to the synthesis of spiroketal systems of the 1,7-dioxaspiro[5.5]undecane and 1,6-dioxaspiro[4.5]decane families is discussed. The key reaction in the approach features oxidation of a suitably substituted furfurol derivative 1 to afford pyranone 2, which subsequently undergoes stereoselective intramolecular ketalization under acidic conditions to furnish spiroketal 3, carrying the 2,6-anti relationship. Analogous methodology is employed to synthesize in a stereoselective fashion model systems for the avermectin spiroketal moieties 9-11 and the pheromones of the olive fruit fly (39 and 40). |
---|---|
Bibliography: | istex:A4C5AF7B853A5A4AC5063B214A42666A3F093BD7 ark:/67375/TPS-XN5WS9J1-V ObjectType-Article-2 SourceType-Scholarly Journals-1 ObjectType-Feature-1 content type line 23 |
ISSN: | 0002-7863 1520-5126 |
DOI: | 10.1021/ja00214a039 |