A synthesis of (-)-mintlactone.
Mintlactone is synthesized in a concise and efficient way by using a highly diastereoselective intramolecular propargylic Barbier reaction, followed by an allenol cyclocarbonylation. Tin(II) chloride is found to be the most effective reagent for the Barbier reaction.
Bates
Roderick W
RW
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, 21 Nanyang Link, Nanyang Technological University, Singapore 637371. roderick@ntu.edu.sg
Sridhar
S
S
D003500:Cyclization; D007783:Lactones / Q000138:chemical synthesis*; D009281:Naphthalenes / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis*; D017971:Tin Compounds / Q000737:chemistry
D007783:Lactones; D009281:Naphthalenes; D013729:Terpenes; D017971:Tin Compounds; C023599:stannous chloride; C110055:allenolic acid; C409815:mintlactone