Synthesis of (-)-berkelic acid.
An extremophilic challenge: Stereospecific condensation of a fully functionalized ketal aldehyde and a 2,6-dihydroxybenzoic acid is the key step in the synthesis of (-)-berkelic acid confirming Fürstner's reassignment of the stereochemistry at C18 and C19, establishing the absolute stereochemistry, and tentatively assigning the stereochemistry at C22.
Wu
Xiaoxing
X
Department of Chemistry, MS 015, Brandeis University, Waltham, MA 02454-9110, USA.
Zhou
Jingye
J
Snider
Barry B
BB
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D062385:Hydroxybenzoates / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000447:Aldehydes; D062385:Hydroxybenzoates; D013141:Spiro Compounds; C520589:berkelic acid; C412605:gamma-resorcylic acid