title: Gold(I)-catalyzed furan-yne cyclizations involving 1,2-rearrangement: efficient synthesis of functionalized 1-naphthols and its application to the synthesis of wailupemycin G.
abstract: Gold-catalyzed cascade cyclization/1,2-rearrangement of 1-(2-furanyl)phenyl propargyl alcohols has been developed, which provides a rapid and efficient access to multisubstituted 1-naphthols bearing an enal or enone moiety with high stereoselectivity. The (Z)- or (E)-stereochemistry can be easily controlled by choosing protected- or non-protected substrates. The utility of the methodology has been illustrated in the first total synthesis of wailupemycin G.
authors: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China), Fax: (+86) 021-64166128.
authors: Yifeng
authors: Y
authors: Chen
authors: Lu
authors: L
authors: Wang
authors: Ning
authors: N
authors: Sun
authors: Xin
authors: X
authors: Xie
authors: Xiaobo
authors: X
authors: Zhou
authors: Haoyi
authors: H
authors: Chen
authors: Yuxue
authors: Y
authors: Li
authors: Yuanhong
authors: Y
authors: Liu
mesh_terms: D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry*; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009284:Naphthols; D011753:Pyrones; C548767:wailupemycin G; C029350:1-naphthol; D006046:Gold
keywords: 1,2-migration; 1-naphthols; furans; gold; homogeneous catalysis