An efficient synthesis of the C27-C45 fragment of lagunamide A, a cyclodepsipeptide with potent cytotoxic and antimalarial properties

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• 作者：Hui-Ming Liu ; Chieh-Yu Chang ; Ya-Chi Lai ; Mei-Due Yang ; Ching-Yao Chang
• 刊名：Tetrahedron: Asymmetry
• 出版年：31 January, 2014
• 年：2014
• 卷：25
• 期：2
• 页码：187-192
• 全文大小：624 K

文摘

An efficient and stereoselective synthesis of the entire C27-C45 moiety of lagunamide A has been achieved from 1-[(4S)-4-benzyl-2-thioxothiazolidin-3-yl]propan-1-one in six steps with 22% overall yield. The key step in the synthesis is an asymmetric acetal aldol reaction featuring the enantioselective addition of a chiral thiazolidinethione-derived titanium enolate to an acetal to establish the stereochemistry at C39.