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1 article(s) from Kanojia, Seema V

A chemoenzymatic synthesis of ceramide trafficking inhibitor HPA-12

Seema V. Kanojia,
Sucheta Chatterjee,
Subrata Chattopadhyay and
Dibakar Goswami

Beilstein J. Org. Chem. 2019, 15, 490–496, doi:10.3762/bjoc.15.42

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Figure 1: Structure of most active HPA-12 isomers, originally proposed (1) and revised (2).

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Scheme 1: Lipase-catalyzed trans-acylation of (±)-4 and subsequent Mitsunobu inversion. Conditions: (i) Zn/TH...

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Scheme 2: Synthesis of azide 9 from (S)-4. Conditions: (i) NaH/Bu₄NI/BnBr/THF/25 °C/4 h; (ii) AD-mix-β/t-BuOH...

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Scheme 3: Attempted synthesis of 2 from 9. Conditions: (i) (a) LiAlH₄ (1 M in THF)/THF/25 °C/3 h, (b) DCC/DMA...

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Scheme 4: Actual synthesis of 2 from 9. Conditions: (i) DDQ/CH₂Cl₂–H₂O 4:1/3 h; (ii) a) LiAlH₄/THF/25 °C/3 h,...

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Published 18 Feb 2019

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