Bioorganic & Medicinal Chemistry Letters

1993

DOI: 10.1016/s0960-894x(00)80331-5

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Design and synthesis of hypertrehalosemic hormoe mimetics

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Cited by 4 publications

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Peptide Mimetic Design with the Aid of Computational Chemistry

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1996

Reviews in Computational Chemistry

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Peptide Mimetic Design with the Aid of Computational Chemistry

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1996

Reviews in Computational Chemistry

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Structure Determination and Total Synthesis of (+)‐16‐Hydroxy‐16,22‐dihydroapparicine

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Chemistry A European J

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Herein, we describe the first asymmetric total synthesis and determination of the relative and absolute stereochemistry of naturally occurring 16-hydroxy-16,22-dihydroapparicine. The key steps include 1) a novel phosphinimine-mediated cascade reaction to construct the unique 1-azabicyclo[4.2.2]decane core, including a pseudo-aminal-type moiety; 2) a highly stereospecific 1,2-addition of 2-acylindole or a methylketone through a Felkin-Anh transition state for the construction of a tetrasubstituted carbon center; and 3) an intramolecular chirality-transferring Michael reaction of the ketoester, with neighboring-group participation, to introduce a chiral center at C15 in the target molecule. In addition, we evaluated the antimalarial activity of synthetic (+)-(15S,16R)-16-hydroxy-16,22-dihydroapparicine and its intermediate against chloroquine-resistant Plasmodium falciparum (K1 strain) parasites.

Synthesis and biological activity of adipokinetic hormone analogues with modifications in the 4–8 region

et al. 2000

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