Synthesis of phosphonate and phostone analogues of ribose-1-phosphates

• Pitak Nasomjai,
• David O'Hagan and
• Alexandra M. Z. Slawin

Beilstein J. Org. Chem. 2009, 5, No. 37, doi:10.3762/bjoc.5.37

• fluorometabolism in S. cattleya. Keywords: 5-fluoro-5-deoxyribose-1-phosphate; fluorometabolite biosynthesis; phosphonates; phostone; ribose-1-phosphate; Introduction Fluoroacetate (1) and 4-fluorothreonine (2) are unusual secondary metabolites in that they contain a fluorine atom. They are elaborated by the

• -phosphate 5 where the linking phosphate oxygen has been replaced by a methylene group and for 9 the fluorine has been replaced by OH (see Figure 1). These phosphonates were considered as candidate inhibitors for either the PNP or the isomerase enzyme, with potential utility as tools to interrogate the

• enzyme which converts 5 to 6 during the biosynthesis. Results and Discussion The target phosphonates 8 and 9 have been prepared by routes A and B as shown in Scheme 1 and Scheme 2 respectively. The routes start either from D-ribonic-γ-lactone (12) or D-ribose (13). For each route the key synthetic steps

DBFOX- Ph/metal complexes: Evaluation as catalysts for enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones

• Takehisa Ishimaru,
• Norio Shibata,
• Dhande Sudhakar Reddy,
• Takao Horikawa,
• Shuichi Nakamura and
• Takeshi Toru

Beilstein J. Org. Chem. 2008, 4, No. 16, doi:10.3762/bjoc.4.16

• fluorination of a wide range of substrates, including β-keto esters, β-keto phosphonates, oxindoles [38][40][43][51][53][56][57]. They have also recently reported the enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones with their extended catalytic system, NiCl2-BINAP/R3SiOTf-lutidine with high

Unexpected degradation of the bisphosphonate P-C-P bridge under mild conditions

• Petri A. Turhanen and
• Jouko J. Vepsäläinen

Beilstein J. Org. Chem. 2008, 4, No. 7, doi:10.1186/1860-5397-4-7

• tetraesters (see Scheme 3 route a), since e.g., 1c, are prepared from phosphites, H-P(O)(OMe)2, and phosphonates, MeCOP(O)(OMe)2, or route b resembling the rearrangement process [19]. The driving force in both reactions is the formation of three charged molecules from one P-C-P compound since this is a highly

New modification of the Perkow reaction: halocarboxylate anions as leaving groups in 3-acyloxyquinoline- 2,4(1H,3H)-dione compounds

• Oldřich Paleta,
• Karel Pomeisl,
• Stanislav Kafka,
• Antonín Klásek and
• Vladislav Kubelka

Beilstein J. Org. Chem. 2005, 1, No. 17, doi:10.1186/1860-5397-1-17

• out[3] (product 2) via the intramolecular Wittig synthesis using a bromoacetyl derivative of the starting 3-hydroxyquinolinediones (1, Scheme 1). Unlike haloalkanes and halocycloalkanes that undergo nucleophilic substitution reaction with trialkyl phosphites to afford the corresponding phosphonates