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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.