Intramolecular carbon-hydrogen insertion: synthesis of (.+-.)-pentalenolactone E methyl ester
β Scribed by Taber, Douglass F.; Schuchardt, Jonathan L.
- Book ID
- 120000004
- Publisher
- American Chemical Society
- Year
- 1985
- Tongue
- English
- Weight
- 238 KB
- Volume
- 107
- Category
- Article
- ISSN
- 0002-7863
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π SIMILAR VOLUMES
The naturally occurruq enantlomer of peatalenolactone E was synthesized as Its levorotatory Me ester 1 starting from (+)-2-ethoxycarbonyl-7,7-ethylenedioxyblcyclo[3.3.0loctan-3-one 3, which was obtarrxl by treatng (?)-3 with baker's yeast. The absolute configuration of pentalenolactone E Me ester wa
Stereospecific 1,4-Addition reaction of lithiated sulfinylallyl anion and enone 2 provided the corresponding 1,4-y-adduct, 7. In seven steps, 7 was converted into octahydro-2methoxy-8,8-dimethylpentalenol[l,6a-c]pyran-5-(6~)-one (9) whose conversion into pentalenolactone E methyl ester (1) has been