title: Construction of Bridged Polycyclic Systems by Polyene Cyclization.
abstract: A stereoselective construction of bridged tri- and tetracyclic systems embedded in some 3,5-dimethylorsellinic acid (DMOA)-derived meroterpenoids was achieved by exploiting a polyene cyclization of suitably functionalized epoxyallylsilanes. Both the olefinic substituent on the epoxide and allylic trimethylsilyl (TMS) group were found to play pivotal roles in the success of the present reaction. The fact that the cyclization of monocyclized byproducts did not proceed strongly suggests that the reaction could be a concerted transformation.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1 Tanabe-dori, Mizuho-ku, Nagoya 467-8603 (Japan).
authors.forename: Keisuke
authors.initials: K
authors.lastname: Suzuki
authors.affiliation: Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1 Tanabe-dori, Mizuho-ku, Nagoya 467-8603 (Japan).
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Yamakoshi
authors.affiliation: Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1 Tanabe-dori, Mizuho-ku, Nagoya 467-8603 (Japan). nakamura@phar.nagoya-cu.ac.jp.
authors.forename: Seiichi
authors.initials: S
authors.lastname: Nakamura
keywords: Lewis acids; bioinspired synthesis; bridged polycycles; cyclization; meroterpenoids