Abstract

Cyclophostin, the cyclipostins and the salinipostins are structurally related cyclic enolphosphate natural products. This mini review describes their isolation, synthesis and biological activities. In addition, the synthesis and biological activities of monocyclic enolphosphate and mono and bicyclic enolphosphonate analogs are presented.

Highlights

  • Medicinal chemists have often turned to nature as a source of bioactive compounds, for anticancer or antimicrobial agents [1,2,3]

  • The mechanism of the anti-mycobacterial was not directly discussed, thewas patent directly discussed, the patent referred to enzymes related to hormone sensitive lipase produced referred to enzymes related to hormone sensitive lipase produced by mycobacterium tuberculosis.by mycobacterium tuberculosis

  • Selective hydrogenation of the vinyl phosphonate (16) using hydrogen over 10% Pd/C poisoned with hydrogenation of the vinyl phosphonate (16) using hydrogen over 10% Pd/C poisoned with pyridine pyridine gave the saturated phosphonates (17), which after selective demethylation, protonation of gave the saturated phosphonates (17), which after selective demethylation, protonation of the resulting salt, and cyclization gave the monocyclic enolphosphonates (18)

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Summary

Introduction

Medicinal chemists have often turned to nature as a source of bioactive compounds, for anticancer or antimicrobial agents [1,2,3]. In a recent review it was reported that of the drugs approved between 1981 and 2010, 34% were based on natural products, either directly or as derivatives [3]. The phosphate moiety is ubiquitous throughout nature and phosphate containing natural products should provide additional opportunities for drug discovery. It is not surprising that over the past 30 over years some very interesting, structurally related, biologically active bicyclic enolphosphates have been isolated from various Streptomyces strains. Their isolation, synthesis and biological activities, and the synthesis and biological activities of monocyclic enolphosphate and mono and bicyclic enolphosphonate analogs are discussed below

Isolation and Structure of Cyclophostin
Isolation of the Cyclipostins
Isolation of the Salinipostins
Stereochemical Nomenclature
Biosynthesis
Synthesis
Synthesis of the Salinipostins
Synthesis of Mono and Bicyclic Phosphonate Analogs
Amberlite
The synthesis of phosphonate analogs
2.10. Synthesis
2.11. Biological
Findings
Conclusions
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