1 article(s) from Westphal, Julia C
- Full Research Paper
- Published 11 Feb 2014
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Graphical Abstract
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Figure 1: Natural products and other bioactive piperidine derivatives of type B.
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Figure 2: Retrosynthetic analysis of piperidines B (X = OH or leaving group, PG = protecting group).
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Scheme 1: Synthesis of the protected amino acids 2. (a) KOH for 1b. b) PG–X = Cbz–Cl (1a–c), Boc2O (1d).
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Scheme 2: Synthesis of hydroxy ketones 7 (R = Me (a), Bn (b), Ph (c) and EtSMe (d); PG = Cbz (a–c), Boc (d)).
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Scheme 3: Synthesis of amides 5e and 5f and ketone 7e.
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Scheme 4: Synthesis of amino alcohols syn-9a–d and oxazolidinone 10a. (for 7a–c conditions A: H2 (1 atm), Pd/...
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Scheme 5: Competition between the Michaelis–Arbuzow process and the desired cyclodehydration of amino alcohol...
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Scheme 6: Initial synthesis of the trans-piperidinol 11a in diminished enantiopurity. aThe amino alcohol 9a o...
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Scheme 7: Synthesis of trans-piperidinol 11a in excellent ee.
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Scheme 8: Synthesis of L-733,060·HCl.
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