Asymmetric Total Synthesis of Cladosporin and Isocladosporin

• Published in: Journal of organic chemistry Vol. 77; no. 13; pp. 5656 - 5663
• Main Authors: Zheng, Huaiji, Zhao, Changgui, Fang, Bowen, Jing, Peng, Yang, Juan, Xie, Xingang, She, Xuegong
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 06.07.2012; Amer Chemical Soc
• Subjects: antibiotics; chemical reactions; Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Isocoumarins - chemical synthesis; Isocoumarins - chemistry; Molecular Structure; Organic chemistry; Physical Sciences; Preparations and properties; research methods; Science & Technology; Stereoisomerism; KETONES; METABOLIC PRODUCTS; PHOSPHORIC-ACID; STEREOSELECTIVE CONSTRUCTION; STEREOCHEMISTRY; MACROLIDE; CIS-2,6-DISUBSTITUTED TETRAHYDROPYRANS; ETHERIFICATION; OXOCARBENIUM IONS; SPIRASTRELLOLIDE; Asymmetric synthesis; Oxygen heterocycle; Relative configuration; Total synthesis

The first asymmetric total syntheses of cladosporin and isocladosporin were accomplished in 8 steps with 8% overall yield and 10 steps with 26% overall yield, respectively. The relative configuration of isocladosporin was determined via this total synthesis.