Journal of Organic Chemistry p. 4683 - 4687 (1990)
Update date:2022-08-10
Topics:
Hudlicky, Tomas
Luna, Hector
Price, John D.
Rulin, Fan
Both enantiomers of the pyrrolizidine alkaloid trihydroxyheliotridane 1 have been prepared in an efficient and stereocontrolled fashion in 10 steps.Key steps involve the microbial oxidation of chlorobenzene with Pseudomonas putida to afford chiral cyclohexadienediol 4 with high enantiomeric excess and its conversion to lactone 7, from which either enantiomer of azide 18 can be prepared.The azides are converted to the title compounds via a <4+1> pyrroline annulation based on an intramolecuular azide-diene cycloaddition/thermal rearrangement.
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