Asymmetric total synthesis of (-)-jorunnamycins A and C and (-)-jorumycin from L-tyrosine.
Three renieramycin-type antitumor alkaloids, (-)-jorunnamycins A (1) and C (2) and (-)-jorumycin (3), have been synthesized by a new convergent approach, which features a highly regio- and stereoselective Pictet-Spengler cyclization to couple the isoquinoline and the trisubstituted phenylalaninol partners. This synthetic strategy opens an economical access to these important antitumor alkaloids with high yields: (-)-jorunnamycin A, as a common precursor to other renieramycin-type alkaloids and their analogues, is obtained with 18.1% overall yield from l-tyrosine.
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, People's Republic of China.
Ruijiao
R
Chen
Hao
H
Liu
Xiaochuan
X
Chen
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003500:Cyclization; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D015363:Quinolones; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D014443:Tyrosine / Q000737:chemistry*
D000470:Alkaloids; D007546:Isoquinolines; D015363:Quinolones; D011809:Quinones; D044005:Tetrahydroisoquinolines; C507297:jorumycin; C584995:jorunnamycin A; C550260:jorunnamycin C; D014443:Tyrosine