Details

Autor(en) / Beteiligte

• Shu, Penghua
• Xiao, Xiong
• Zhao, Yueqi
• Xu, Yang
• Yao, Wang
• Tao, Jinyi
• Wang, Hao
• Yao, Guangmin
• Lu, Zimin
• Zeng, Jing
• Wan, Qian

Titel

Interrupted Pummerer Reaction in Latent-Active Glycosylation: Glycosyl Donors with a Recyclable and Regenerative Leaving Group

Ist Teil von

• Angewandte Chemie International Edition, 2015-11, Vol.54 (48), p.14432-14436

Auflage

International ed. in English

Ort / Verlag

Weinheim: WILEY-VCH Verlag

Erscheinungsjahr

2015

Quelle

MEDLINE

Beschreibungen/Notizen

• Latent O‐glycosides, 2‐(2‐propylthiol)benzyl (PTB) glycosides, were converted into the corresponding active glycosyl donors, 2‐(2‐propylsulfinyl)benzyl (PSB) glycosides, by a simple and efficient oxidation. Treatment of the PSB donor and various acceptors with triflic anhydride provided the desired glycosides in good to excellent yields. The leaving group, which was activated by an interrupted Pummerer reaction, can be recycled (PSB‐OH) and regenerated as the precursor (PTB‐OH). A natural hepatoprotective glycoside, leonoside F, was efficiently synthesized in a convergent [3+1] manner with this newly developed method. The present total synthesis also led to a structural revision of this phenylethanoid glycoside. Actively latent: An efficient glycosylation enabled by an interrupted Pummerer reaction was successfully achieved. The active glycosyl donor possessing a recyclable and regenerative leaving group was obtained from a simple oxidation of the corresponding latent precursor. This strategy allowed the total synthesis and structural revision of the natural product leonoside F.