Catalytic asymmetric hetero-Diels–Alder route to a key intermediate for the synthesis of calyxin L

Washio, Takuya; Nambu, Hisanori; Anada, Masahiro et al.

Tetrahedron Asymmetry, 2007, 18(21), 2606-2612

Permalink : https://hdl.handle.net/2115/32289

このアイテムのアクセス数:1,360件（2026-08-18 08:27 集計）

ファイル	フォーマット	サイズ	閲覧回数	説明
T-Asym	pdf	413 KB	1,632

アクセス権	open access
URI	https://hdl.handle.net/2115/32289
タイトル	Catalytic asymmetric hetero-Diels–Alder route to a key intermediate for the synthesis of calyxin L
著者	Washio, Takuya ; Nambu, Hisanori ; Anada, Masahiro ; Hashimoto, Shunichi
著者名 Washio, Takuya
e-Rad_Researcher 80399956 著者名 Nambu, Hisanori
e-Rad_Researcher 90344473 著者名 Anada, Masahiro
e-Rad_Researcher 80107391 著者名 Hashimoto, Shunichi
言語	英語
発行日	2007-10-22
出版者	Elsevier
収録物名	Tetrahedron Asymmetry
巻(号)	18(21)
ページ	2606-2612
抄録	A catalytic asymmetric formal synthesis of diarylheptanoid natural product calyxin L has been achieved by incorporating an enantio- and diastereoselective hetero-Diels-Alder (HDA) reaction, a Suzuki-Miyaura coupling, and a stereocontrolled catalytic hydrogenation of 2,4,6-trisubstituted dihydropyran as the key steps. The HDA reaction between 4-(4-benzyloxyphenyl)-2-triethylsilyloxy-1,3-butadiene and (4-benzenesulfonyloxyphenyl)propynal catalyzed by dirhodium(II) tetrakis[(R)-3-(benzene-fused-phthalimido)-2-piperidinonate], Rh_{2}(R-BPTPI)_{4}, provided cis-2,6-disubstituted tetrahydropyran-4-one in 91% yield with 91% ee.
資源タイプ	学術雑誌論文
出版タイプ	Accepted Manuscript
PISSN	0957-4166
関連情報	URI http://www.sciencedirect.com/science/journal/09574166
関連情報 (isVersionOf)	出版社版DOI https://doi.org/10.1016/j.tetasy.2007.10.025