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Total synthesis of zaragozic acid C by an aldol-based strategy

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Please use this identifier to cite or link to this item:http://hdl.handle.net/2115/727

Title: Total synthesis of zaragozic acid C by an aldol-based strategy
Authors: Nakamura, Seiichi1 Browse this author
Sato, Hiroki2 Browse this author
Hirata, Yuuki3 Browse this author
Watanabe, Nobuhide4 Browse this author
Hashimoto, Shunichi5 Browse this author →KAKEN DB
Authors(alt): 中村, 精一1
佐藤, 浩樹2
平田, 勇樹3
渡邉, 信英4
橋本, 俊一5
Keywords: Zaragozic acids
Aldol reaction
α-Keto ester
Silyl ketene thioacetal
Internal ketalization
Issue Date: 21-Nov-2005
Publisher: Elsevier
Journal Title: Tetrahedron
Volume: 61
Issue: 47
Start Page: 11078
End Page: 11106
Publisher DOI: 10.1016/j.tet.2005.09.030
Abstract: A total synthesis of zaragozic acid C by a convergent strategy is described in which the key features include (1) the simultaneous creation of the C4 and C5 quaternary stereogenic centers by a Sn(OTf)2-promoted aldol coupling reaction between an α-keto ester and a silyl ketene thioacetal derived from L- and D-tartaric acids, respectively, (2) the direct introduction of lithium acetylide as the C1 side chain equivalent onto the fully functionalized aldehyde, and (3) construction of the bicyclic core structure by acid-catalyzed internal ketalization under kinetically controlled conditions.
Relation: http://www.sciencedirect.com/science/journal/00404020
Type: article (author version)
URI: http://hdl.handle.net/2115/727
Appears in Collections:薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 中村 精一

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