Divergent Synthetic Route to Oxidized Benzofulvene Sesquiterpenoids: Protecting‐Group‐Free Total Synthesis of Nicotianasesterpenes A, B, and a Polygonum Sesquiterpenoid | Zendy

Jeong Myeonggyo | Zendy; Lee Hyunkee | Zendy; Kim Gibeom | Zendy; Jo Jeyun | Zendy; Chang Jae Won | Zendy; Jung Jee H. | Zendy; Suh YoungGer | Zendy; Yun Hwayoung | Zendy

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Divergent Synthetic Route to Oxidized Benzofulvene Sesquiterpenoids: Protecting‐Group‐Free Total Synthesis of Nicotianasesterpenes A, B, and a Polygonum Sesquiterpenoid

Author(s) -

Jeong Myeonggyo,

Lee Hyunkee,

Kim Gibeom,

Jo Jeyun,

Chang Jae Won,

Jung Jee H.,

Suh YoungGer,

Yun Hwayoung

Publication year - 2019

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201901351

Subject(s) - chemistry , aldol condensation , stereoselectivity , total synthesis , aldol reaction , enamine , stereochemistry , polygonum , protecting group , halogenation , substrate (aquarium) , organic chemistry , catalysis , traditional medicine , medicine , alkyl , oceanography , geology

A divergent approach toward the protecting‐group‐free total synthesis of oxidized benzofulvene sesquiterpenoids is described. Highlight of our synthesis includes regio‐ and stereoselective assembly of the common intermediate 9 by the orchestrated application of a Pd(0)‐catalyzed reductive dehalogenation, a solvent‐free methylenation, and a vinylogous Stork enamine aldol condensation in a substrate‐controlled manner. The advanced intermediate 9 was efficiently transformed to nicotianasesterpenes A, B, and a polygonum sesquiterpenoid, respectively.

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