Palladium-Catalyzed Sequential Arylation and Allylic Alkylation of Highly Functionalized Ketones: A Concise Synthesis of Mesembrine

Zhao, Yongchun; Zhou, Yong‐Gui; Liang, Leilei; Yang, Xiaodong; Du, Fengxiang; Li, Liang; Zhang, Hongbin

doi:10.1021/ol802608r

Cited by 49 publications

(26 citation statements)

References 42 publications

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“…Synthetic applications of 3-alkoxy-2-cyclohexenones toward the pursuit of natural products have been well documented [1–4]. Traditionally, 3-alkoxy-2-cyclohexenones have been prepared from 1,3-cyclohexadiones under a variety of conditions [5–6].…”

Section: Resultsmentioning

confidence: 99%

Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones

Hylden¹,

Uzelac²,

Ostojic³

et al. 2011

Beilstein J. Org. Chem.

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Section: Resultsmentioning

confidence: 99%

Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones

Hylden¹,

Uzelac²,

Ostojic³

et al. 2011

Beilstein J. Org. Chem.

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“…The Boc‐group was removed under acidic conditions and methyl iodide used for methylation. Conjugate reduction using stoichiometric amounts of lithium in liquid ammonia completed the total synthesis of (−)‐mesembrine …”

Section: Discussionmentioning

confidence: 99%

Total Synthesis of Mesembrine – The Construction of Quaternary Stereocenters by Gold‐Catalyzed Diyne Desymmetrization

Czekelius

2018

Israel Journal of Chemistry

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This review gives an overview on synthetic methodology developed for the synthesis of the naturally occurring alkaloid mesembrine. Its all‐carbon‐substituted quaternary stereocenter has fuelled creativity in the application of ex‐chiral‐pool‐synthesis, chiral auxiliaries, and asymmetric catalysis alike. The gold‐catalyzed desymmetrization of 1,4‐diynes has been demonstrated as a selective method for the enantioselective preparation of methylene pyrrolidines incorporating a quaternary stereocenter. The applicability of this method has therefore been demonstrated in the context of a mesembrine total synthesis.

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“…A major focus of our research group is the use of metal mediated sequential reactions to assemble the key structure units of the target molecules [ 60 – 63 ]. Our synthesis of the HPI alkaloids initiated in the early 2008.…”

Section: Introductionmentioning

confidence: 99%

“…Our synthesis of the HPI alkaloids initiated in the early 2008. We successfully developed a sequential reaction for the synthesis of mesembrine [ 60 ] and esermethole [ 61 ] using palladium chemistry. In 2012, we developed a copper catalyzed arylation of o -bromoanilides assisted by a remote sulfinylamide or carbamate auxiliary [ 62 ].…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of Dimeric HPI Alkaloids

Shen

Zhou

et al. 2016

Nat. Prod. Bioprospect.

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In this paper, we report a full account of the synthesis of dimeric hexahydropyrroloindole alkaloids and its analogues. The key feature of our new strategy is the novel catalytic copper (10 %) mediated intramolecular arylations of o-haloanilides followed by intermolecular oxidative dimerization of the resulting oxindoles in one pot. This sequential reaction leads to the key intermediates for the synthesis of (+)-chimonanthine, (+)-folicanthine, (−)-calycanthine and (−)-ditryptophenaline.Graphical Abstract In the presence of catalytic amount of cuprous iodide (10 %), an intramolecular arylation of o-haloanilides followed by an intermolecular oxidative dimerization of the resulting oxindoles leads to a common intermediate for the synthesis of (+)-chimonanthine, (+)-folicanthine and (−)-calycanthine. Based on this cascade sequence, we also developed a flexible strategy towards the asymmetric syntheses of dimeric HPI alkaloids (−)-ditryptophenaline and its analogues.Electronic supplementary materialThe online version of this article (doi:10.1007/s13659-016-0092-8) contains supplementary material, which is available to authorized users.

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Palladium-Catalyzed Sequential Arylation and Allylic Alkylation of Highly Functionalized Ketones: A Concise Synthesis of Mesembrine

Cited by 49 publications

References 42 publications

Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones

Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones

Total Synthesis of Mesembrine – The Construction of Quaternary Stereocenters by Gold‐Catalyzed Diyne Desymmetrization

Total Synthesis of Dimeric HPI Alkaloids

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