Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 23, Pages 8891-8900Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo061660a
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Funding
- NCI NIH HHS [CA-034303, R01 CA034303-25, R01 CA034303] Funding Source: Medline
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An efficient synthetic strategy for installation of the two vicinal quaternary carbon centers of the communesins is reported. Key steps include the O-allylation/Claisen rearrangement of spirolactone systems, which are formed by tandem intramolecular Heck cyclization/carbonylation. Substituent and solvent effects on the stereochemical outcome of the Claisen rearrangements have been examined. The stereochemical assignment of the allyl spirolactone previously reported as 17 has now been revised to 31, which has the communesin relative configuration at the quaternary carbons. Key C-allyl spirolactone 59 bearing functional handles required for the communesin core has been constructed with a 9.8:1 diastereomer ratio.
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