A rapid and efficient access to renieramycin-type alkaloids featuring a temperature-dependent stereoselective cyclization

作者：Liu, Hao; Chen, Ruijiao; Chen, Xiaochuan^*

来源：Organic and Biomolecular Chemistry, 2014, 12(10): 1633-1640.

DOI：10.1039/c3ob42209g

• ASYMMETRIC TOTAL-SYNTHESIS
• CARIBBEAN TUNICATE
• ANTITUMOR-ACTIVITY
• PROTECTING GROUPS
• (-)-JORUMYCIN
• CHEMISTRY
• REMOVAL
• DRUG
• ECTEINASCIDIN-743
• TRANSFORMATION

A flexible and practical protocol for the asymmetric synthesis of renieramycin-type antitumor alkaloids is described, in which the stereoselective Pictet-Spengler cyclization of amino ester 16 and aldehyde 15 by regulating temperature and the automatic lactamization after N-deprotection of the cyclization product are exploited to rapidly construct the common pentacyclic framework. (-)-Renieramycin G and (-)-jorunnamycin A, as representative members of the two subgroup renieramycin-type alkaloids, are obtained in 19 steps from L-tyrosine with 15.8% and 14.3% overall yield respectively.

• 出版日期2014
• 单位四川大学; 济宁医学院