153046-00-5Relevant academic research and scientific papers
Total Synthesis of (+)-Hyacinthacine A1Using a Chemoselective Cross-Benzoin Reaction and a Furan Photooxygenation-Amine Cyclization Strategy
Parmar, Karnjit,Haghshenas, Pouyan,Gravel, Michel
, p. 1416 - 1421 (2021)
We report the shortest synthesis of glycosidase inhibitor (+)-hyacinthacine A1 using a highly chemoselective N-heterocyclic carbene-catalyzed cross-benzoin reaction as well as a furan photooxygenation-amine cyclization strategy. This is the first such cyclization on a furylic alcohol, an unprecedented reaction due to the notorious instability of the formed intermediates. The photooxygenation strategy was eventually incorporated into a three-step one-pot process that formed the requisite pyrrolizidine framework of (+)-hyacinthacine A1.
A facile synthetic route to diazepinone derivatives via ring closing metathesis and its application for human cytidine deaminase inhibitors
Kim, Minkyoung,Gajulapati, Kondaji,Kim, Chorong,Jung, Hwa Young,Goo, Jail,Lee, Kyeong,Kaur, Navneet,Kang, Hyo Jin,Chung, Sang J.,Choi, Yongseok
supporting information, p. 11443 - 11445 (2013/01/15)
A variety of diazepinone derivatives were prepared from α-amino acids and amino alcohols by a new synthetic methodology based on ring closing metathesis as a key step. The diazepinones were coupled with ribose derivatives to afford novel diazepinone nucleosides. Among them, (4R)-1-ribosyl-4-methyl-3, 4-dihydro-1H-1,3-diazepin-2(7H)-one (3) showed a potent inhibitory effect (Ki = 145.97 ± 4.87 nM) against human cytidine deaminase.
A concise stereoselective synthesis of orthogonally protected lanthionine and β-methyllanthionine
Cobb, Steven L.,Vederas, John C.
, p. 1031 - 1038 (2008/01/03)
Lantibiotics such as nisin are active against most Gram-positive bacteria and constitute an important class of antibacterial agents. These ribosomally synthesized peptides contain either one or both of the unusual amino acids meso-lanthionine (m-Lan) or β
Stereoselective synthesis of β-amino alcohols: Practical preparation of all four stereomers of N-PMB-protected sphingosine from L- and D-serine
Chung, Sung-Kee,Lee, Jae-Mok
, p. 1441 - 1444 (2007/10/03)
Serine was efficiently converted to the N-p-methoxybenzyl (PMB) protected α'-amino enone derivative 6, which was reduced with Zn(BH4)2 to the corresponding anti-β-amino alcohol in >96% de. On the other hand, N- PMB-N-Boc-protected α'-amino enone derivative 8 was reduced by NaBH4 to syn-product with a diastereoselectivity of ca. 90%.
