104417-89-2Relevant academic research and scientific papers
Hydroxylamine-Mediated Anthrapyranone Formation, Solving 5-exo/6-endo Issue toward Synthesis of Pluramycin-Class Antibiotics
Shimura, Jun,Ando, Yoshio,Suzuki, Keisuke
, p. 175 - 179 (2020/01/02)
In our synthetic study on pluramycin-class antibiotics, an unexpected issue arose, i.e., unfavorable regioselectivity of 5-exo rather than 6-endo cyclization to form the pyranone ring. The issue was solved by an addition-elimination process of a phenol-ynone substrate. AZADOL was specifically effective, enabling the first synthesis of saptomycinone H.
Synthesis of pluraflavin A "aglycone"
Wright, Benjamin J. D.,Hartung, John,Peng, Feng,Van De Water, Ryan,Liu, Haibo,Tan, Quen-Hui,Chou, Ting-Chao,Danishefsky, Samuel J.
supporting information; experimental part, p. 16786 - 16790 (2009/04/14)
The "aglycone" of pluraflavin A (2) has been synthesized. The key features of this synthesis include a 1,3-dipolar cycloaddition between a nitrile oxide (cf. 14) and an olefin (22) to yield an isoxazoline followed by subsequent conversion into the γ-pyrone of pluraflavin A. The epoxide moiety linked to the pyrone is installed prior to Diels-Alder installation of the D ring, which allows access to a number of potentially active cytotoxic intermediates en route to the final compound. The preliminary in vitro results of two such compounds are also included with the racemic title compound exhibiting cytotoxicity in the nanomolar range.
Total Synthesis of (+/-)-Citreoviral, based on a Biogenetic Model, and Formal Synthesis of (+/-)-Citreoviridin
Bowden, Martin C.,Patel, Prakash,Pattenden, Gerald
, p. 1947 - 1950 (2007/10/02)
The total synthesis of (+/-)-citreoviral, which co-occurs with citreoviridin, citreoviridinol, and citreodiol in Penicillium citreoviride, is described.The synthesis is based on a biogenetic model, and has as a key feature the elaboration of the dihydroxytetrahydrofuranyl ring portion 10 by an acid-catalysed cyclisation of the central epoxy alcohol intermediate 9 which is derived in ten steps from methyl tiglate.
SUBSTRATE SPECIFICITY AND ENANTIOSELECTIVITY OF PENICILLINACYLASE CATALYZED HYDROLYSIS OF PHENACETYL ESTERS OF SYNTHETICALLY USEFUL CARBINOLS
Fuganti, Claudio,Grasselli, Piero,Servi, Stefano,Lazzarini, Ameriga,Casati, Paolo
, p. 2575 - 2582 (2007/10/02)
Penicillinacylase from E. coli, immobilized on Eupergit C beads catalyzes the hydrolysis in water/CH3CN 10:1, at pH 7.5 and 23 deg C, of a set of O-phenylacetate esters of primary carbinols.The highest enantioselectivity is observed in the case of the 2,2-dimethyl-1,3-dioxolane-4-methanols structurally related to the penicillin (1) framework.Minor modifications of this basic structure are not altering the acceptability by the enzyme, but significantly decrease the enantioselectivity of the hydrolysis, as does the use of benzene as solvent and Sepharose-bound enzyme.
ENANTIOSELECTIVE SYNTHESIS OF (+)-CITREOVIRAL USING ASYMMETRIC HYDROXYLATION OF TIGLATE ESTERS
Hatakeyama, Susumi,Matsui, Yumiko,Suzuki, Masahiro,Sakurai, Kuniya,Takano, Seiichi
, p. 6485 - 6488 (2007/10/02)
A microbial metabolite (+)-citreoviral has been synthesized enantio- and stereo-selectively using newly developed asymmetric hydroxylation of tiglate esters for the construction of the key chiral building block.
