A convergent stereocontrolled total synthesis of (-)-terpestacin.
A stereocontrolled total synthesis of (-)-terpestacin has been achieved starting from (R)-(-)-carvone as a chiral pool and (E,E)-farnesol via a highly convergent approach. Thus, (R)-(-)-carvone was transformed into the cyclopentanone segment through a series of high yielding operations with the proper setup of all the stereochemical centers while (E,E)-farnesol was converted into the other requisite building block via a series of high yielding reactions. The cyclopentanone intermediate was both selectively enolized and alkylated at room temperature to yield the desired coupling product, which provided the natural product upon further transformations.
Laboratory of Molecular Engineering, Guangzhou Institutes of Biomedicine and Health, The Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530, China.
Yehua
Y
Jin
Fayang G
FG
Qiu
D000478:Alkylation; D001203:Ascomycota / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000737:chemistry; D000081005:Cyclohexane Monoterpenes; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry; D005204:Farnesol / Q000138:chemical synthesis / Q000737:chemistry; D039821:Monoterpenes / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D001688:Biological Products; D001643:Bridged Bicyclo Compounds; D000081005:Cyclohexane Monoterpenes; D003517:Cyclopentanes; D039821:Monoterpenes; C080890:terpestacin; C007201:cyclopentanone; D005204:Farnesol; C006923:carvone