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

TETRAHEDRON

卷:71

Article

Kutsumura, Noriki^1,2  Matsubara, Yusuke²  Honjo, Takuya²  Ohgiya, Tadaaki³  Nishiyama, Shigeru⁴  Saito, Takao² 

[1] Univ Tsukuba, Int Inst Integrat Sleep Med WPI IIIS, Tsukuba, Ibaraki 3058577, Japan

[2] Tokyo Univ Sci, Dept Chem, Fac Sci, Shinjuku Ku, Tokyo 1628601, Japan

[3] Kowa Co Ltd, Tokyo New Drug Res Labs, Div Pharmaceut, Tokyo 1890022, Japan

[4] Keio Univ, Dept Chem, Fac Sci & Technol, Kohoku Ku, Yokoyama 2238522, Japan

关键词: Total synthesis;    One-pot regioselective bromination;    Suzuki-Miyaura coupling;    Germacranes;    Natural product;   

DOI  :  10.1016/j.tet.2015.02.093

来源: Elsevier

【 摘 要 】

The first total synthesis of (-)-5,6-seco-germacrane lactone has been achieved. The synthetic highlight of our approach includes sp(2)-sp(3) 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. (C) 2015 Elsevier Ltd. All rights reserved.

【 授权许可】

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