Mechanistic investigation and implications of a sacrificial aniline for the tandem cascade synthesis of 4-aza-podophyllotoxin analogues

作者：Jeedimalla Nagalakshmi; Johns Jennifer; Roche Stephane P^*

来源：Tetrahedron Letters, 2013, 54(44): 5845-5848.

DOI：10.1016/j.tetlet.2013.08.071

• Natural product-mimetic scaffolds
• Heterolignans
• 4-Aza-podophyllotoxin Cascade reaction
• Mechanistic investigation

Mechanistic investigations were pursued to determine a plausible mechanism in the cascade reaction involving tetronic acid with aldehydes and anilines to generate the 4-aza-2,3-dehydropodophyllotoxin core structure. The mechanistic driven hypothesis paved the way for a new reaction design using for the first time a sacrificial electron deficient aniline leading to an optimized cascade protocol (up to threefold yield improvement) for the synthesis of novel 4-aza-2,3-dehydropodophyllotoxin analogues. Published by Elsevier Ltd.

• 出版日期2013-10-30