First diastereoselective synthesis of (-)-methyl thyrsiflorin A, (-)-methyl thyrsiflorin B acetate, and (-)-thyrsiflorin C.
An efficient procedure for the synthesis of scopadulan diterpenes, using (+)-podocarp-8(14)-en-13-one 13 as starting material, is reported. This procedure has been used for the diastereoselective synthesis of (-)-methyl thyrsiflorin A (8), (-)-methyl thyrsiflorin B acetate (9), and (-)-thyrsiflorin C (7). Key steps in our strategy are the intramolecular cyclopropanation of diazoketone 19 and the regioselective cleavage of the cyclopropane ring.
Arnó
M
M
Departamento de Química Orgánica, Facultad de Química, Universidad de Valencia, C/ Dr. Moliner 50, E- 46100 Burjassot, Valencia, Spain.
González
M A
MA
Marín
M L
ML
Zaragozá
R J
RJ
D004224:Diterpenes / Q000138:chemical synthesis*; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry*; D013057:Spectrum Analysis; D013237:Stereoisomerism
D004224:Diterpenes; C415030:methyl thyrsiflorin A; C415029:methyl thyrsiflorin B; C415031:thyrsiflorin C