60059-09-8Relevant academic research and scientific papers
TOTHAL SYNTHESIS OF MIMOCIN
Matsuo, Keizo,Okumura, Masao,Tanaka, Kuniyoshi
, p. 1339 - 1340 (1982)
Mimocin (1), an isoquinolinequinone antibiotic, is synthesized in ten steps starting from 2,3,6-trimethoxytoluene.
Practical synthesis of tricyclic lactam model of antitumor renieramycin-saframycin natural products
Yokoya, Masashi,Fujino, Akiya,Yaguchi, Ayako,Yamazaki, Miku,Saito, Naoki
, p. 802 - 815 (2017/04/10)
A practical synthesis of the tricyclic lactam model compound of antitumor renieramycin-saframycin natural product starting from 2-hydroxy-4,5-dimethoxy-3-methylbenzaldehyde in eleven steps was described. A tosyl group was used for protection of a phenol d
Catalytic Asymmetric Crotylation of Aldehydes: Application in Total Synthesis of (-)-Elisabethadione
O'Hora, Paul S.,Incerti-Pradillos, Celia A.,Kabeshov, Mikhail A.,Shipilovskikh, Sergei A.,Rubtsov, Aleksandr E.,Elsegood, Mark R. J.,Malkov, Andrei V.
, p. 4551 - 4555 (2015/03/18)
A new, highly efficient Lewis base catalyst for a practical enantio- and diastereoselective crotylation of unsaturated aldehydes with E- and Z-crotyltrichlorosilanes has been developed. The method was employed as a key step in a novel asymmetric synthesis of bioactive serrulatane diterpene (-)-elisabethadione. Other strategic reactions for setting up the stereogenic centers included anionic oxy-Cope rearrangement and cationic cyclization. The synthetic route relies on simple, high yielding reactions and avoids use of protecting groups or chiral auxiliaries.
Improvements in aldol reactions with diketopiperazines
Gonzalez, Juan Francisco,De La Cuesta, Elena,Avendano, Carmen
, p. 1589 - 1597 (2007/10/03)
Precipitation of products by using dichloromethane as solvent permits an efficient aidol-type reaction between 1,4-diacetyl-2,5-piperazinedione and aromatic aldehydes catalyzed by KtBuO/tBuOH independently of the electrophilic character of the aryl ring. A simple method to obtain 3-methyl-2,4,5-trimethoxybenzaldehyde is also reported.
Saframycin synthetic studies
Shawe, Thomas T.,Liebeskind, Lanny S.
, p. 5643 - 5666 (2007/10/02)
A conceptually simple and direct synthetic route to racemic saframycyn B, a bis-isoquinoline quinone antitumor antibiotic, was studied relying on transformations of a key C-2 symmetric intermediate.
Lewis Acid Mediated Claisen-Type Rearrangement of Aryl Dienyl Ethers
Maruyama, Kazuhiro,Nagai, Naoshi,Naruta, Yoshinori
, p. 5083 - 5092 (2007/10/02)
Rearrangement of aryl pentadienyl ethers in the presence of BF3*OEt2 affords pentadienyl phenols in good yields without formation of the corresponding rearranged products.The mechanism of this rearrangement was studied by deuterium labeling and cross-coupling reactions.The scope and limitations of the rearrangement are discussed.
