Expeditious construction of (+)-mintlactone via intramolecular hetero-Pauson-Khand reaction.
(+)-Mintlactone, a bicyclic monoterpene natural product, has been efficiently assembled from (-)-citronellol in three steps. The synthesis features nitrous acid-induced formal isopropylidene "demethanation" and the molybdenum-mediated intramolecular hetero-Pauson-Khand reaction.
Gao
Peng
P
Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China 200032.
Xu
Peng-Fei
PF
Zhai
Hongbin
H
D000080462:Acyclic Monoterpenes; D000475:Alkenes; D007783:Lactones / Q000138:chemical synthesis*; D008982:Molybdenum; D039821:Monoterpenes / Q000737:chemistry; D009608:Nitrous Acid; D013729:Terpenes / Q000138:chemical synthesis*
D000080462:Acyclic Monoterpenes; D000475:Alkenes; D007783:Lactones; D039821:Monoterpenes; D013729:Terpenes; D008982:Molybdenum; C013658:propylene; C007078:citronellol; D009608:Nitrous Acid; C409815:mintlactone