Complementary routes for the stereoselective synthesis of functionalized benzoquinolizidine targets

Allin, Steven M.; Duffy, Liam J.; Page, Philip C. Bulman; McKee, Vickie; Edgar, Mark; McKenzie, Michael J.; Amat, Mercedes; Bassas, Oriol; Santos, Maria M. M.; Bosch, Joan

doi:10.1016/j.tetlet.2006.06.035

Cited by 24 publications

(7 citation statements)

References 10 publications

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“…[1] Although several asymmetric methods for the construction of optically active quinolizidine derivatives have been developed, these strategies are in general target specific, multistep syntheses relying on starting material from the chiral pool. [2,3] In contrast to syntheses based on molecules from the chiral pool, only a few strategies that relay on asymmetric catalysis have been described. [4,5] The development of new stereoselective, efficient, and short routes to this class of compound would therefore open up new opportunities for natural product synthesis and medicinal chemistry.…”

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confidence: 99%

Asymmetric Alkaloid Synthesis: A One‐Pot Organocatalytic Reaction to Quinolizidine Derivatives

Franzén

Fisher

2009

Angewandte Chemie

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confidence: 99%

Asymmetric Alkaloid Synthesis: A One‐Pot Organocatalytic Reaction to Quinolizidine Derivatives

Franzén

Fisher

2009

Angewandte Chemie

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“…24 Interestingly, cyclization of a thioamide, via a thioimidate salt, provides access to regioisomeric indoloquinolizidines with the connectivity and stereochemistry required for the synthesis of natural products, for instance dihydrocorynantheine. The removal of the hydroxymethyl substitutent can be performed by a radical decarboxylation of the corresponding carboxylic acid,25 as outlined in Scheme .…”

Section: Discussionmentioning

confidence: 99%

Chiral Oxazolopiperidone Lactams: Versatile Intermediates for the Enantioselective Synthesis of Piperidine‐Containing Natural Products

Escolano

Amat

Bosch

2006

Chemistry A European J

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187

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Phenylglycinol-derived oxazolopiperidone lactams are exceptionally versatile building blocks for the enantioselective construction of structurally diverse piperidine-containing natural products and bioactive compounds. These lactams are readily available in both enantiomeric series by cyclocondensation of the chiral amino alcohol with a delta-oxo acid derivative and allow the substituents to be introduced at the different ring positions in a regio- and stereocontrolled manner, providing access to enantiopure polysubstituted piperidines bearing virtually any type of substitution pattern, and also quinolizidines, indolizidines, perhydroquinolines, hydroisoquinolines, as well as complex indole alkaloids. Of particular interest are cyclocondensation reactions with racemic or prochiral delta-oxo (di)acid derivatives in processes involving dynamic kinetic resolution and/or differentiation of enantiotopic or diastereotopic ester groups, as they directly lead to lactams that already incorporate the carbon substituents on the heterocyclic ring. The use of (S)-3,4-dimethoxyphenylalaninol or (S)-tryptophanol in the above cyclocondensation reactions expands the potential and the scope of the methodology, providing a straightforward route to enantiopure benzo[a]- and indolo[2,3-a]quinolizidines.

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“…Titanium tetrachloride, gave exclusively the benzoquinolizidine derivative 49 displaying cis relative stereochemistry, as required in targets such as protoemetinol (35).…”

Section: Scheme 12mentioning

confidence: 99%

“…In collaboration with Amat and Bosch, our teams have also developed an entry to functionalized benzoquinolizidine derivatives that allows the efficient preparation of targets with complementary relative stereochemistries [35]. The first approach is through conjugate addition to an α,β-unsaturated tetrahydroisoquinoline substrate 45 (Scheme 11).…”

Section: Scheme 10mentioning

confidence: 99%

Asymmetric N-Acyliminium Cyclization as an Approach to Heterocyclic Natural Product Synthesis

Gaskell

Duffy

Allin

2008

Natural Product Communications

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Dedicated to Prof. Wilfred R. Chan for his inspiration and dedication to natural products chemistry. This paper describes the development of a highly stereoselective N-acyliminium cyclization protocol for the construction of a range of non-racemic heterocyclic templates. Due to the nature of this review, we have focused primarily on developments made within our own research group, but have included relevant and noteworthy contributions in the same area from others, most notably the research groups of Amat, Bosch and Lete. As a result, we apologize in advance for the omission of much excellent work carried out by many other talented researchers in this field.

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Complementary routes for the stereoselective synthesis of functionalized benzoquinolizidine targets

Cited by 24 publications

References 10 publications

Asymmetric Alkaloid Synthesis: A One‐Pot Organocatalytic Reaction to Quinolizidine Derivatives

Asymmetric Alkaloid Synthesis: A One‐Pot Organocatalytic Reaction to Quinolizidine Derivatives

Chiral Oxazolopiperidone Lactams: Versatile Intermediates for the Enantioselective Synthesis of Piperidine‐Containing Natural Products

Asymmetric N-Acyliminium Cyclization as an Approach to Heterocyclic Natural Product Synthesis

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