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1 article(s) from Saha, Nemai

Enantioselective synthesis of polyhydroxyindolizidinone and quinolizidinone derivatives from a common precursor

Nemai Saha and
Shital K. Chattopadhyay

Beilstein J. Org. Chem. 2014, 10, 3104–3110, doi:10.3762/bjoc.10.327

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Graphical Abstract

Figure 1: Selected polyhydroxyindolizidine and quinolizidines of importance.

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Figure 2: Target bicyclic imino sugars Ia and Ib from a common intermediate IV.

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Scheme 1: Reagents and conditions: (i) Zn/AcOH, rt, 1 h, 86%. (ii) TBSOTf, DIPEA, CH₂Cl₂, −5 °C, 1 h, 91%. (i...

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Scheme 2: Reagents and conditions: (i) OsO₄, NMO, acetone/water, rt, 12 h, 96%. (ii) NaH, THF, BnBr, Bu₄NI, 0...

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Figure 3: Selected nOe correlations (A) and coupling constants (B) for compound 15.

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Figure 4: ¹H,¹H COSY spectrum of compound 15.

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Scheme 3: Reagents and conditions: (i) OsO₄, NMO, acetone/water, 6 h, 95%. (ii) NaH, THF, BnBr, Bu₄NI, 0 °C t...

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Figure 5: Selected nOe correlations and part NOESY spectrum of compound 23 in D₂O (600 MHz).

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Published 22 Dec 2014

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