478-36-4Relevant academic research and scientific papers
Total synthesis of enantiopure 1,3-dimethylpyranonaphthoquinones including ventiloquinones E, G, L and eleutherin
Tewierik, Leonie M.,Dimitriadis, Christian,Donner, Christopher D.,Gill, Melvyn,Willems, Brendan
, p. 3311 - 3318 (2006)
A new synthetic approach to enantiopure pyranonaphthoquinones is described. (S)-Mellein 10, prepared in 6 steps from (S)-propylene oxide 16, is converted stereospecifically to the (1R,3S)-dimethylpyran 15. The pyran 15 is then converted to the benzoquinone 14, which undergoes regiospecific Diels-Alder reactions with a variety of oxygenated butadienes to give pyranonaphthoquinones including ventiloquinones E, G, L, eleutherin and ent-deoxyquinone A. The Royal Society of Chemistry 2006.
ANTIMICROBIAL AGENTS FROM HIGHER PLANTS: TWO DIMETHYLBENZISOCHROMANS FROM KARWINSKIA HUMBOLDTIANA
Mitscher, Lester A.,Gollapudi, Sitaraghav R.,Oburn, David S.,Drake, Steven
, p. 1681 - 1684 (1985)
Two new antimicrobial dimethylbenzisochromans were isolated from the roots of Karwinskia humboldtiana together with the known 7-acetyl-6,8-dimethoxy-3-methyl-1-naphthol.The structures and absolute configurations were determined by spectroscopic examination and by chemical transformation to the known quinones eleutherin and 7-methoxyeleutherin.Key Word Index - Karwinskia humboldtiana; Rhamnaceae; karwinaphthol A and B; 2-acetyl-6,8-dimethoxy-3-methyl-1-naphthol; eleutherin and 7-methoxyeleutherin; antimicrobial activity.
Application of a dual fries-Claisen protocol to access pyranonaphthoquinone natural products
Duffy, Liam J.,Garcia-Torres, Jason,Jones, Raymond C.F.,Elsegood, Mark R.J.,Allin, Steven M.
, p. 185 - 188 (2013/02/25)
In this paper we describe the application of a recently developed dual Fries-Claisen protocol as a novel synthetic approach to the pyranonaphthoquinone natural products eleutherin and isoeleutherin. Georg Thieme Verlag Stuttgart · New York.
A concise and improved synthesis of (+)-eleutherin, (+)-allo-eleutherin and a formal synthesis of (+)-nocardione B
Fernandes, Rodney A.,Chavan, Vijay P.,Mulay, Sandip V.
experimental part, p. 487 - 492 (2011/06/11)
A concise and improved stereoselective synthesis of (+)-eleutherin, (+)-allo-eleutherin and the formal synthesis of (+)-nocardione B is described. The synthesis is based on a Doetz benzannulation and an improved oxa-Pictet-Spengler cyclization as the key steps. The synthesis is achieved in six steps in overall yields of 18% for eleutherin and 20% for allo-eleutherin.
A short enantioselective synthesis of (+)-eleutherin, (+)-allo-eleutherin and a formal synthesis of (+)-nocardione B
Fernandes, Rodney A.,Chavan, Vijay P.,Ingle, Arun B.
scheme or table, p. 6341 - 6343 (2009/04/07)
A short enantioselective synthesis of (+)-eleutherin, (+)-allo-eleutherin and the formal synthesis of (+)-nocardione B is described. The synthesis is completed in six steps in overall yields of 8% for eleutherin and 14% for allo-eleutherin. The synthetic strategy features an efficient combination of the D?tz annulation reaction with a chiral alkyne and an oxa-Pictet Spengler reaction as the keys steps in the stereodivergent synthesis of (+)-eleutherin and (+)-allo-eleutherin. The synthesis of (S)-(+)-2-(2′-hydroxypropyl)-5-methoxy-1,4-naphthoquinone entails the formal synthesis of (+)-nocardione B.
A short enantioselective synthesis of the topoisomerase II inhibitor (+)-eleutherin
Gibson, Jennifer S.,Andrey, Olivier,Brimble, Margaret A.
, p. 2611 - 2613 (2008/02/13)
A Hauser-Kraus annulation was used as a key step for the concise enantioselective synthesis of the topoisomerase II inhibitor (+)-eleutherin. Georg Thieme Verlag Stuttgart.
