A novel stereocontrolled approach to eudesmanolides: total synthesis of (+/-)-gallicadiol and (+/-)-isogallicadiol.
[reaction: see text] A novel approach for the stereocontrolled synthesis of eudesmanolides was developed based on a quasi-biomimetic strategy starting from a functionalized oxabicyclic template, as shown above, by which the first total syntheses of gallicadiol (6) and isogallicadiol (7) were achieved. The key elements of the synthesis include: (1) a facile and stereospecific synthesis of a functionalized epoxy aldehyde intermediate; (2) a mild Lewis acid-mediated stereoselective ene cyclization; and (3) a stereocontrolled gamma-lactonization.
Li
Wei-Dong Z
WD
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, China. liwd@lzu.edu.cn
Gao
Zhang-Hua
ZH
D019306:Artemisia / Q000737:chemistry; D018360:Crystallography, X-Ray; D007783:Lactones / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D007783:Lactones; D012717:Sesquiterpenes; C476916:eudesmanolide; C509579:gallicadiol