Studies directed toward the synthesis of terreulactone A: rapid construction of the A, B, C rings.
[structure: see text]. An efficient, rapid synthesis of the A, B, C rings of terreulactone A is described. Key steps in the synthesis include a diastereoselective benzylic acid rearrangement to create the desired quaternary center at C2 and a mild bromolactonization to assemble the lactonic ring A.
Liu
Haibo
H
Department of Chemistry, Columbia University, Havemeyer Hall, New York, New York 10027, USA.
Siegel
Dionicio R
DR
Danishefsky
Samuel J
SJ
D001230:Aspergillus / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry
D001688:Biological Products; D012717:Sesquiterpenes; C514119:terreulactone A