57575-19-6Relevant academic research and scientific papers
First Total Synthesis of the Proposed Structure of Pandangolide 1
Show, Krishanu,Gonnade, Rajesh G.,Kumar, Pradeep
, p. 3352 - 3364 (2018)
The first total synthesis of the proposed structure of pandangolide 1 is reported. The synthesis was carried out using both an organocatalytic approach and a chiral-pool approach. The required stereochemistry at C-3 and C-5 was installed by using an organocatalytic aldol reaction and a stereoselective ketone reduction. The construction of the 12-membered core was achieved by 2-methyl-6-nitrobenzoic anhydride-mediated Shiina lactonization. The structure of target molecule was confirmed unambiguously by single-crystal X-ray analysis, but the optical rotation and NMR spectroscopic data of the synthetic pandangolide 1 were found to be inconsistent with the natural product.
A stereoselective approach for the total synthesis of (-)-tadanalactam from acetonide-d-glucose
Konda, Saidulu,Kurva, Bhaskar,Nagarapu, Lingaiah,Dattatray, Akkewar M.
, p. 834 - 836 (2015/03/03)
A stereoselective and realistic approach for the total synthesis of naturally occurring δ-lactam (-)-tadanalactam, has been accomplished from the commercially existing acetonide-d-glucose involving Birch reduction, Pinnick oxidation, Staudinger reaction,
Synthesis of a furanosyl-pyranone derivative related to the tri-o-heterocyclic core of herbicidins
Hsu, Ching-Yun,Lee, I-Chi,Lico, Larry S.,Uang, Biing-Jiun,Hung, Shang-Cheng
, p. 421 - 425 (2012/08/08)
A new compound that is structurally related to the undecose ring structure of herbicidins has been prepared. The synthesis of this novel furanosyl-pyranone derivative was made possible through the regioselective reductive ring-opening of a 3,5-O-benzylidene-D-xylofuranose and the hetero-Diels-Alder reaction of an aldehyde and a Danishefsky-type diene. The highly functionalized pyranone derivative can be a useful precursor for the synthesis of herbicidins.
Synthesis of carba analogues of deoxy-4-C-(hydroxymethyl)-hexopyranoses, intermediates in the synthesis of carbocyclic nucleosides
Hrebabecky, Hubert,Holy, Antonin
, p. 785 - 798 (2007/10/03)
3-O-Benzyl-1,2-O-isopropylidene-α-D-glucofuranose-5,6-O-sulfate (1) was treated with sodium salt of dimethyl malonate to obtain, after hydrolysis, methyl 5-(3-O-benzyl-1,2-O-isopropylidene-α-D-erythrofuranos-4-yl)-2- oxotetrahydrofuran-3-carboxylate (3) w
OXIRANE RINGS: STUDIES AND APPLICATIONS OF A NEW CHEMO AND REGIO SELECTIVE REDUCTIVE OPENING OF EPOXIDES
Bonini, Carlo,Fabio, Romano Di,Sotgiu, Giovanni,Cavagnero, Silvia
, p. 2895 - 2904 (2007/10/02)
The straightforward reductive opening of 1,2 epoxides to alcohols was studied and applied to several significant compounds.The reaction, which proceeds via the nucleophilic opening of the oxirane ring and the subsequent free radical dehalogenation, shows an excellent chemical yield as well as chemo and regioselectivity.This reaction was also applied to a chiral α,β-epoxyester.
