2011
DOI: 10.1021/jo102178h
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The Shortest Synthetic Route to Puromycin Analogues Using a Modified Robins Approach

Abstract: We are reporting on the utility of commercial vinyl isocyanate for a practical synthetic route from adenosine to N(6)-bis-demethylpuromycin in seven steps and 65% overall yield. A clean one-pot conversion of 3'-bromo-2'-carbamoyl derivative 8 to 3'-amino-3'-deoxyadenosine derivative 10 is the main feature of this synthetic pathway. This synthesis is the shortest synthetic route toward 3'-(aminoacylamido)deoxyadenosines to date.

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Cited by 7 publications
(3 citation statements)
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“…Some reports on the construction of an oxazolidinone ring from bromohydrin and isocyanate have been published. 9,10 In both cases, NaH was used for cyclization to construct the oxazolidinone ring. However, there are no examples of the application of this approach to indole and azaindole derivatives.…”
Section: Letter Synlettmentioning
confidence: 99%
“…Some reports on the construction of an oxazolidinone ring from bromohydrin and isocyanate have been published. 9,10 In both cases, NaH was used for cyclization to construct the oxazolidinone ring. However, there are no examples of the application of this approach to indole and azaindole derivatives.…”
Section: Letter Synlettmentioning
confidence: 99%
“…To understand the structure–activity relationships (SAR) and to develop drug candidates as well as probes for investigating the translation process, many efforts have been given to the chemical synthesis of puromycin and hygromycin A derivatives. Especially, the total synthesis of hygromycin A has been achieved by Ogawa et al in 1989 and by Donohoe et al in 2009, respectively, , and a synthesis of the 1,2- trans -furanoside analogue of hygromycin A was accomplished by Trost et al In contrast, study toward the synthesis of A201A, which demands incorporation/elaboration of the unique hexofuranose D unit with an exocyclic enol ether moiety, has never been reported. Here, we communicate the first synthesis of this complex nucleoside antibiotic ( 1 ).…”
mentioning
confidence: 99%
“…Treatment of 15 with aqueous dimethylamine in refluxing ethanol led to replacement of the 6-chloride together with cleavage of the 2′,5′- O -benzoyl groups; subsequent protection of the resulting diol with TES group afforded 16 (76% for two steps). Azide 16 was then converted into the 3′-amino-3′-deoxyadenosine 17 (Ph 3 P, THF, H 2 O, 50 °C, 92%), which has been the key precursor in the synthesis of puromycin derivatives …”
mentioning
confidence: 99%