69172-20-9Relevant academic research and scientific papers
Enantioselective total synthesis of ligraminol d and ligraminol e
Kumbhar, D. D.,Mane, Baliram B.,Waghmode, Suresh B.
, p. 2285 - 2289 (2019/12/11)
As a part of our ongoing research on the synthesis of bioactive constituents or molecules by using an organocatalytic approach, enantioselective total syntheses of ligraminol D and ligraminol E were achieved starting from a commercially available nonchiral aldehyde. Key steps in this synthesis were an asymmetric α-aminoxylation of an aldehyde and a Mitsunobu reaction.
An Efficient Enantioselective Synthesis of Natural Gingerols, the Active Principles of Ginger
Ramesh Reddy,Wadavrao, Sachin B.,Yadav,Venkat Narsaiah
, p. 1009 - 1017 (2015/11/23)
A straightforward synthesis of (S)-gingerols 1-3 has been described. The requisite stereogenic center in the target molecules was introduced by Sharpless asymmetric dihydroxylation using a chiral complex, AD-mix β. This route is simple and efficient to prepare the products in very good yields.
First total synthesis and reassignment of absolute configuration of diosniponol A and B
Yadav,Singh, Vinay K.,Thirupathaiah,Reddy, A. Bal
, p. 4427 - 4429 (2014/08/05)
Enantioselective first total synthesis of diosniponol A and B has been achieved starting from commercially available vanillin. Wittig reaction, Keck allylation, and Prins cyclization reactions are the key steps involved in the target synthesis.
A natural product inspired tetrahydropyran collection yields mitosis modulators that synergistically target CSE1L and tubulin
Voigt, Tobias,Gerding-Reimers, Claas,Tran, Tuyen Thi Ngoc,Bergmann, Sabrina,Lachance, Hugo,Sch?lermann, Beate,Brockmeyer, Andreas,Janning, Petra,Ziegler, Slava,Waldmann, Herbert
supporting information, p. 410 - 414 (2013/02/23)
A Prins cyclization between a polymerbound aldehyde and a homoallylic alcohol served as the key step in the synthesis of tetrahydropyran derivatives. A phenotypic screen led to the identification of compounds that inhibit mitosis (as seen by the accumulation of round cells with condensed DNA and membrane blebs; see picture). These compounds were termed tubulexins as they target the CSE1L protein and the vinca alkaloid binding site of tubulin.
Synthesis of gingerol and diarylheptanoids
Sabitha, Gowravaram,Srinivas, Chitti,Reddy, Teega Rammohan,Yadagiri, Kurra,Yadav, Jhillu Singh
, p. 2124 - 2133 (2012/03/27)
The synthesis of gingerol 1 and related compounds 2-5 along with diarylheptanoids 6-8 has been accomplished using a Keck allylation, Crimmins' aldol reaction, aldehyde coupling with acetylene, and chelation controlled reductions as the key reactions. The absolute configuration of these molecules was confirmed by preparing their acetonide derivatives and by comparison of the NMR data with natural compounds.
Synthesis of diarylheptanoids, (5S)-5-acetoxy-1,7-bis(4-hydroxy-3- methoxyphenyl)-3-heptanone and (3S,5S)-3,5-diacetoxy-1,7-bis(4-hydroxy-3- methoxyphenyl)heptane
Sabitha, Gowravaram,Chandrashekhar, Gajangi,Yadagiri, Kurra,Yadav, Jhillu Singh
experimental part, p. 1729 - 1735 (2012/01/14)
The total syntheses of the first examples of diarylheptanoid natural products (5S)-5-acetoxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3-heptanone 1, and (3S,5S)-3,5-diacetoxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane 2 isolated from the rhizomes of Zingiber officinale were accomplished using Sharpless epoxidation and cross-metathesis reactions as the key steps.
Structure and Synthesis of New Phenolic Amides from Piper nigrum L.
Inatani, Reiko,Nakatani, Nobuji,Fuwa, Hidetsugu
, p. 667 - 674 (2007/10/02)
New phenolic amides, N-trans-feruloyl piperidine (4a), N-5-(4-hydroxy-3-methoxyphenyl)-2E,4E-pentadienoyl piperidine (5a) and N-5-(4-hydroxy-3-methoxyphenyl)-2E-pentenoyl piperidine (6a) were isolated from the fruit of white pepper (Piper nigrum L.).The f
