Journal
ORGANIC LETTERS
Volume 11, Issue 20, Pages 4640-4643Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol901896c
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Funding
- NSERC
- FQRNT
- Syngenta (Basel, Switzerland)
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An efficient, high-yielding strategy has been developed for the asymmetric total synthesis of seven norditerpenoid dilactones known for their diverse biological properties. The three key steps employed to obtain a tricyclic lactone intermediate Involved a Morita-Baylis-Hillman reaction, the stereocontrolled construction of a gamma-lactone through bromolactonization, and an efficient catalytic Reformatsky-type reaction. Access to CJ-14,445, LL-Z1271 gamma, oidiolactones A, B, C, and D, and nagilactone F was possible from a common intermediate. Structures and stereochemistry were determined by X-ray analysis.
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