Novel approach for the stereocontrolled construction of eudesmane skeleton: a concise synthesis of (+/-)-balanitol.
[structure: see text] A novel method for the stereocontrolled construction of the eudesmane ring system based on a cationic cyclization is presented, and the approach is exemplified in a short and efficient total synthesis of (+/-)-balanitol (2).
Zhang
Z
Z
National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
Li
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WD
Li
Y
Y
D002384:Catalysis; D003500:Cyclization; D006865:Hydrogenation; D007202:Indicators and Reagents; D007564:Japan; D008968:Molecular Conformation; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry; D012717:Sesquiterpenes; D045787:Sesquiterpenes, Eudesmane; D013237:Stereoisomerism
D007202:Indicators and Reagents; D009281:Naphthalenes; D012717:Sesquiterpenes; D045787:Sesquiterpenes, Eudesmane; C434311:balanitol; C015872:eudesmane