Beilstein J. Org. Chem.2023,19, 687–699, doi:10.3762/bjoc.19.50
of two ring bonds. This review includes the recent syntheses of seven to fourteen-membered phostam, phostone, and phostine derivatives.
Keywords: azaphosphaheterocycle; oxaphosphaheterocycle; phostam; phostine; phostone; Introduction
Phostams, phostones, and phostines are a class of important
prepared, while numerous five-membered γ-phostams [11][12], γ-phostones and γ-phostines [13], and six-membered δ-phostams [14][15][16], δ-phostones [17][18] and δ-phostines [17][19][20] have been synthesized via various synthetic strategies. In comparison with common ring size phostam, phostone, and
phostine derivatives, less attention has been paid to the synthesis of medium and large phostam, phostone, and phostine derivatives. They are also biologically active compounds, such as inhibitors of the human farnesyl pyrophosphate synthase [21][22], antitumor agents [23], and hapten for the production of
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Graphical Abstract
Figure 1:
Biologically active agents and chiral ligands containing medium and large phostams, phostones, and ...
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
biosynthesis system, and as inert candidate substrate analogues for enzyme co-crystallisation studies. We also report the synthesis of the cyclic phostone analogues 10 and 11 (Figure 1), which were viewed also as potential substrate analogues for co-crystallisation studies, particularly with the isomerase
] to generate the cyclic phostones 10 and 11 respectively. In each case this conversion could be conveniently followed by a change in the 31P-NMR resonance of 27 ppm (phosphonate) to 44 ppm, characteristic of a cyclic phostone. Purification by chromatography allowed the recovery of the phostones 10 and
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Graphical Abstract
Scheme 1:
Biosynthetic pathway from fluoride ion to fluoroacetate 1 and 4-fluorothreonine 2 in S. cattleya [2].