Abstract:[reaction: see text] The stereocontrolled synthesis of malayamycin A, a novel naturally occurring bicyclic C-nucleoside of the perhydrofuropyran type, is described.
“…39). [888][889][890] A bacterial translocase inhibitor, A-94964A contains two unidentified sugars, 2 0 -deoxy-2 0 -aminohexosyl-1phosphate (234) and a hexose (334), attached to a riboocturonic acid (233) appended to N-1 of uracil. 891,892 13.1.2 Cytosine-derived nucleosides.…”
Section: Nucleosides and Nucleosidederived Compoundsmentioning
A systematic analysis of all naturally-occurring glycosylated bacterial secondary metabolites reported in the scientific literature up through early 2013 is presented. This comprehensive analysis of 15 940 bacterial natural products revealed 3426 glycosides containing 344 distinct appended carbohydrates and highlights a range of unique opportunities for future biosynthetic study and glycodiversification efforts.
“…39). [888][889][890] A bacterial translocase inhibitor, A-94964A contains two unidentified sugars, 2 0 -deoxy-2 0 -aminohexosyl-1phosphate (234) and a hexose (334), attached to a riboocturonic acid (233) appended to N-1 of uracil. 891,892 13.1.2 Cytosine-derived nucleosides.…”
Section: Nucleosides and Nucleosidederived Compoundsmentioning
A systematic analysis of all naturally-occurring glycosylated bacterial secondary metabolites reported in the scientific literature up through early 2013 is presented. This comprehensive analysis of 15 940 bacterial natural products revealed 3426 glycosides containing 344 distinct appended carbohydrates and highlights a range of unique opportunities for future biosynthetic study and glycodiversification efforts.
“…The malayamycin synthesis story is all the more relevant when one considers that the natural product itself was isolated over a decade ago,47d and it remained in the proprietary domain until the opportunity arose for structural confirmation through synthesis 48e. 130 The potential for biological activity for natural and unnatural analogues of compounds relating to malaymycin A with applications for human use remains to be explored.…”
A “reorientation” of the concept of total synthesis of natural products emphasizes a biology‐inspired, chemistry‐driven approach without compromising the sanctity of basic research and the noble objectives of co‐worker training in an academic setting. Structure‐based organic synthesis provides a unique framework to capitalize on data gleaned from the bioactivity of natural products in conjunction with X‐ray crystallography, molecular modeling, and NMR spectroscopy for the design and synthesis of new drug prototypes.
“…Soon after its disclosure, a first total synthesis of malayamycin A (20; see Scheme 4) was published by the group of Hanessian and the relative and absolute stereochemistry could be confirmed. 13 Consequently, joint efforts were undertaken by the Hanessian group and Syngenta scientists to access synthetic derivatives of 20 and establish an SAR of this compound class. 14 The synthesis of malayamycin A started from D-ribonolactone (21) which was converted into intermediate 22 by acetal protection of the hydroxyl groups followed by addition of 5-lithio-2,4-dimethoxypyrimidine to the lactone moiety.…”
Natural products play an important role as lead structures for the identification of novel active ingredients in crop protection. As it is the case in the pharmaceutical industry, however, many crop protection companies have substantially decreased their in-house efforts in natural product exploration. Therefore, joint projects with academic research groups become more and more important in the field. This review describes several examples for successful collaborations in the field of fungicidal natural products.
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