Pinnatoxin A の全合成

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概要

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• The first total synthesis of pinnatoxin A (1), a Ca<SUP>2+</SUP>-channel activator isolated in 1995 by Uemura and co-workers from the shellfish <I>Pinna muricata</I>, is reported. The synthetic plan was based on Uemuras biosynthetic proposal, and consists of an intramolecular Diels-Alder reaction for construction of the G-ring as well as the macrocycle, followed by imine formation to establish the 6, 7-spiro-ring system. During this investigation, factors controlling the stereochemistry of the BCD bis-spiroketal ring system were investigated, and the chemoselectivity and efficiency of the Ni (II) /Cr (II) -mediated coupling protocol were demonstrated. This synthesis has also established the absolute stereochemistry of natural pinnatoxin A as the antipode of structure 1.

• 2000-09-01

著者

• 長澤 和夫

  ハーバード大・化学生物化学

• 長澤 和夫

  ハーバード大学化学生物化学科

関連論文

• 4 Pinnatoxin Aの全合成(口頭発表の部)
• Pinnatoxin A の全合成

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