A Highly Stereoselective Total Synthesis of (+)-9-epi-Dictyostatin

作者：Zanato Chiara; Pignataro Luca; Ambrosi Andrea; Hao Zhongyan; Gennarri Cesare^*

来源：European Journal of Organic Chemistry, 2010, (30): 5767-5771.

DOI：10.1002/ejoc.201001018

• Antitumor agents
• Asymmetric synthesis
• Macrocycles
• Natural products
• Total synthesis

The total synthesis of (+)-9-epi-dictyostatin (1b), a diastereomer of the antimitotic marine-sponge-derived macro-tide (-)-dictyostatin (1a), was achieved by creating 11 stereogenic centers and 4 stereogenic double bonds with a high level of stereocontrol. The yield for the 29-step longest linear sequence from Roche ester was 1.53%. The final key steps to this unnatural product were the vinylzincate C10-C26 addition to aldehyde C1-C9 (leading surprisingly to a complete stereoselectivity for the 9R-epimer), followed by Yamaguchi macrolactonization and global deprotection.

• 出版日期2010-10