Journal Article Total synthesis of (−)-5,6-seco-germacrane lactone

Kutsumura, Noriki  ,  Matsubara, Yusuke  ,  Honjo, Takuya  ,  Ohgiya, Tadaaki  ,  Nishiyama, Shigeru  ,  Saito, Takao

71 ( 16 )  , pp.2382 - 2386 , 2015-04 , Elsevier
The first total synthesis of (−)-5,6-seco-germacrane lactone has been achieved. The synthetic highlight of our approach includes sp2–sp3 Suzuki–Miyaura cross coupling of a vinyl bromide and an alkyl 9-BBN derivative. The vinyl bromide was easily prepared from the chiral lactonic building block using a one-pot regioselective bromination. The asymmetric carbon center of the alkyl boron compound was formed using the zirconium-catalyzed carbomagnesation of 2,5-dihydrofuran.

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