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

• Nakamura, Seiichi

• Sato, Hiroki

• Hirata, Yuuki

• Watanabe, Nobuhide

• Hashimoto, Shunichi

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.

Journal

• Tetrahedron

  Tetrahedron 61 (47), 11078-11106, 2005-11-21

  Elsevier

Keywords

• Zaragozic acids
• Aldol reaction
• α-Keto ester
• Silyl ketene thioacetal
• Internal ketalization

Details

• CRID: 1050564288923058176
• NII Article ID: 120000962955
• HANDLE: 2115/727
• ISSN: 00404020
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • CiNii Articles