166322-32-3Relevant academic research and scientific papers
A Formal Total Synthesis of (±)-Enterolactone
Srikrishna,Danieldoss,Venkateswarlu,Sattigeri
, p. 864 - 869 (2007/10/03)
A radical cyclization based methodology has been applied for the formal total synthesis of (±)-enterolactone (1), the first lignan isolated from human source. Bromoacetalization reaction of the cinnamyl alcohols 7 and 13 using ethyl vinyl ether and NBS, generated the bromoacetals 8 and 15. The 5-exo-trig radical cyclization reaction of the bromoacetals 8 and 15 with in situ generated catalytic tri-n-butyltin hydride and AIBN furnished a 3 : 2 diastereomeric mixture of the cyclic acetals 9 and 16. Sonochemically accelerated Jones oxidation of the cyclic acetals 9 and 16 yielded the γ-butyrolactones 10 and 12 completing the formal total synthesis of (±)-enterolactone. Alternatively radical cyclization of the bromoacetate 17 furnished a 1 : 2 mixture of the lactone 10 and the reduced product 18.
Radical cyclisation methodology to lignans: Synthesis of (+/-)-enterolactone
Srikrishna, A.,Venkateswarlu, S.,Danieldoss, S.,Sattigeri, J. A.
, p. 679 - 681 (2007/10/03)
Synthesis of enterolactone, the first lignan of human origin, starting from 3-methoxycinnamyl alcohol employing a 5-exo-trig radical cyclisation reaction of mixed bromoacetal as the key step is described.
