Biomimetic synthesis of ent-(-)-azonazine and stereochemical reassignment of natural product.
The first total synthesis of ent-(-)-azonazine has been accomplished using a hypervalent iodine-mediated biomimetic oxidative cyclization to construct the highly strained core. Based on the results from the completed synthesis, both the relative and absolute configurations of natural (+)-azonazine were revised.
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
Ji-Chen
JC
Zhao
Shun-Ming
SM
Yu
Yun
Y
Liu
Zhu-Jun
ZJ
Yao
D001230:Aspergillus / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D032701:Biomimetics; D018360:Crystallography, X-Ray; D003500:Cyclization; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D001688:Biological Products; D004151:Dipeptides; C555149:azonazine