Total Synthesis of the Proposed Structure of Trichodermatide A

详细信息    查看全文

• 作者：Eddie Myers ; Elena Herrero-G贸mez ; Irina Albrecht ; Jennifer Lachs ; Peter Mayer ; Matti Hanni ; Christian Ochsenfeld ; Dirk Trauner
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：October 17, 2014
• 年：2014
• 卷：79
• 期：20
• 页码：9812-9817
• 全文大小：335K
• ISSN：1520-6904

文摘

A short total synthesis of the published structure of racemic trichodermatide A is reported. Our synthesis involves a Knoevenagel condensation/Michael addition sequence, followed by the formation of tricyclic hexahydroxanthene-dione and a diastereoselective bis-hydroxylation. The final product, the structure of which was confirmed by X-ray crystallography, has NMR spectra that are very similar, but not identical, to those of the isolated natural product. Quantum chemically computed ¹³C shifts agree well with the present NMR measurements.