Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 16, Pages 6245-6252Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo901221a
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Funding
- NIGMS NIH HHS [GM-50151, R01 GM050151-16, R01 GM050151] Funding Source: Medline
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A Kiyooka aldol condensation of an aldehyde with a trimethylsilyl ketene acetal and the oxazaborolidinone prepared from N-Ts-(S)-valine gives two of the four possible aldol adducts, which were oxidized and deprotected to complete the synthesis of (-)-berkelic acid and (-)-22-epi-berkelic acid. This synthesis establishes the absolute stereochemistry and assigns the stereochemistry at C-22. A biosynthetic pathway is proposed that is consistent with the known absolute stereochemistry at the quaternary carbon of spiciferone A, spicifernin, and berkelic acid and provides a simple explanation for the differing stereochemistry at C-18 and C-19 of spicifernin and berkelic acid.
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