391208-04-1Relevant articles and documents
Total synthesis of natural (?)- and unnatural (+)-Melearoride A
Reed, Carson W.,Fulton, Mark G.,Nance, Kellie D.,Lindsley, Craig W.
, p. 743 - 745 (2019)
This communication details the first total synthesis of the 13-membered macrolide, (?)-Melearoride A, as well as unnatural (+)-Melearoride A. The synthesis features a concise 13 step synthesis (11 steps longest linear sequence) that offers flexible stereo-control and multiple opportunities for unnatural analog synthesis to delve into antifungal SAR. The route features a cuprate addition, an Evans asymmetric alkylation, and a ring-closing metathesis (RCM) to close the 13-membered macrocyclic core.
A catalytic approach to (R)-(+)-muscopyridine with integrated self-clearance
Fuerstner, Alois,Leitner, Andreas
, p. 308 - 311 (2003)
The integration of various metal-catalyzed reactions into a one-pot processes opens an unprecedentedly short and efficient route to the odoriferous alkaloid (R)-(+)-muscopyridine. Importantly, it is shown how metathesis can be used for a most convenient self-clearance of a product mixture (see scheme; OTf= CF3SO3).
Remote Arylative Substitution of Alkenes Possessing an Acetoxy Group via β-Acetoxy Elimination
Kakiuchi, Fumitoshi,Kochi, Takuya,Kumagai, Takaaki,Muto, Kazuma
supporting information, p. 24500 - 24504 (2021/10/19)
Palladium-catalyzed remote arylative substitution was achieved for the reaction of arylboronic acids with alkenes possessing a distant acetoxy group to provide arylation products having an alkene moiety at the remote position. The use of β-acetoxy elimination as a key step in the catalytic cycle allowed for regioselective formation of unstabilized alkenes after chain walking. This reaction was applicable to various arylboronic acids as well as alkene substrates.
COMPOUNDS THAT INHIBIT MCL-1 PROTEIN
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Page/Page column 2280; 2381, (2017/09/15)
Provided herein are myeloid cell leukemia 1 protein (Mcl-1) inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula I, and pharmaceutically acceptable salts thereof and pharmaceutical compositions containing the compounds. The compounds and compositions provided herein may be used, for example, in the treatment of diseases or conditions, such as cancer.
Synthesis of (R)- and (S)- muscone
Fujimoto, Satoko,Yoshikawa, Keisuke,Itoh, Masamichi,Kitahara, Takeshi
, p. 1389 - 1392 (2007/10/03)
(R)-(-)-Muscone (3-methylcyclopentadecanone, 1) the key perfumery component isolated from the male musk deer, Moschus moschiferus,* was synthesized from the easily available chiral building block, (R)-3-tert-butoxycarbonyl-2- methylpropanoic acid (2), by employing ring-closing olefin metathesis (RCM). Antipode (+)-1 was also synthesized in a similar manner from tert-butyl (S)-3-methoxycarbonylbutanoate (10). *(a) Walbaum, H. J. J. Prakt. Chem., 73, 488 (1906); (b) Ruzicka, L., Further considerations on the constitution of muscone. Helv. Chim. Acta, 9, 715, 1008-1017 (1926).
