Asymmetric Total Syntheses of Ansamacrolactams (+)-Q-1047H-A-A and (+)-Q-1047H-R-A

作者：Yang, Shouliang; Xi, Yumeng; Zhu, Rong; Wang, Lin; Chen, Jiahua^*; Yang, Zhen

来源：Organic Letters, 2013, 15(4): 812-815.

DOI：10.1021/ol400038h

• ORGANIC-SYNTHESIS
• TETRAPETALONE-A
• ALDOL ADDITIONS
• STREPTOMYCES SP
• SAMARIUM DIIODIDE
• TETRACYCLIC CORE
• NATURAL-PRODUCTS
• DRUG DISCOVERY
• LANTHANIDES
• RING

The total syntheses of ansamacrolactams (+)-Q-1047H-A-A (16) and (+)-Q-1047H-R-A (17) have been achieved for the first time In 17 steps, leading to the reassignment of the relative stereochemistries and absolute configurations of their natural counterparts. The key steps In the synthetic work included an asymmetric chelation-controlled vinylogous Mukaiyama aldol reaction for the stereoselective synthesis of the syn-aldol adduct 7b and an intramolecular SmI2-mediated Reformatsky reaction for the formation of the macrocyclic lactam 14.

• 出版日期2013-2-15
• 单位北京大学; 北京大学深圳研究生院