2005
DOI: 10.1021/jo0484070
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Chemoenzymatic Asymmetric Total Synthesis of Phosphodiesterase Inhibitors:  Preparation of a Polycyclic Pyrazolo[3,4-d]pyrimidine from an Acylnitroso Diels−Alder Cycloadduct-Derived Aminocyclopentenol

Abstract: [reaction: see text] Enzymatic resolution of Boc-protected 4-aminocyclopenten-1-ol 4c gave both enantiomers 5c and 6c in high ee. Boc removal and separate condensation with chloropyrazolopyrimidine 18 provided elaborated 1,4-aminocyclopentenol derivatives 20 and 26, respectively. Separate treatment of 20 and 26 with Pd(0) under basic conditions induced cyclization to unsaturated polycycles 22 and 27, which, upon catalytic hydrogenation, were transformed to new cyclopentane-containing pyrazolopyrimidines 24 and… Show more

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Cited by 35 publications
(23 citation statements)
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“…A palladium-catalyzed decarboxylative amination of allyl carbamates was described [668]. (89) Palladium-catalyzed N-allylations were used to prepare novel carbocyclic nucleoside analogs [669], a polycyclic pyrazolo [3,4-d]pyrimidine [670], deoxymannojirimycin [671], (−)-norsecurine [672], gizzerosine [136] and tetrahydroisoquinolines [673].…”
Section: Carbon-heteroatom Bond-forming Reactions Using Heteroatom Numentioning
confidence: 99%
“…A palladium-catalyzed decarboxylative amination of allyl carbamates was described [668]. (89) Palladium-catalyzed N-allylations were used to prepare novel carbocyclic nucleoside analogs [669], a polycyclic pyrazolo [3,4-d]pyrimidine [670], deoxymannojirimycin [671], (−)-norsecurine [672], gizzerosine [136] and tetrahydroisoquinolines [673].…”
Section: Carbon-heteroatom Bond-forming Reactions Using Heteroatom Numentioning
confidence: 99%
“…13e,20 These conditions proved far more effective than [Pd]-catalyzed hydrogenation. 15 This new diamination methodology, in conjunction with N–O reduction, may well prove useful for the synthesis of 3,4-diamino-1-alcohols such as those found in bioactive natural products.…”
mentioning
confidence: 99%
“…The importance of biological activities of pyrimidinone derivative (6) has resulted in the development of several synthetic methods [23,24], where these method suffers from several disadvantages such as vigorous conditions, long reaction times and low yields [25,26].…”
Section: Scheme-iimentioning
confidence: 99%