Stereodivergent total synthesis of chlorofusin and its all seven chromophore diastereomers. Issue 2 (14th January 2015)

• Record Type: Journal Article
• Authors: Qiu, Hai-Bo; Qian, Wen-Jian; Yu, Shun-Ming; Yao, Zhu-Jun
• Is Part Of: Tetrahedron. Volume 71:Issue 2(2015)
• Page Start: 370
• Page End: 380
• Publication Date: 2015-01-14
• Subjects: Chlorofusin -- Total synthesis -- Stereodivergent synthesis -- Azaphilone -- p53-MDM2 interaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2014.10.062
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Chlorofusin (1 ), one of few natural antagonists against p53-MDM2 interactions, is a naturally biogenetic hybrid composed of a 27-membered nonacyclopeptide and a unique chromophore through the hydrocarbon linkage with ornithine. In this article, we describe our recent achievement, in details, of developing a convenient stereodivergent route for parallel total synthesis of chlorofusin (1 ) and its all seven chromophore diastereomers (1a –1g ) in enantiopure forms, starting from a common racemic azaphilone precursor10 . The newly developed total synthesis shows the great advantages of economy, scalability, stable intermediates, high yields, ease of HPLC-free operations and reduplication. Graphical abstract: