Exploring the Reactivity of Chiral Glycidic Amides for Their Applications in Synthesis of Bioactive Compounds

Sarabia, Francisco; Vivar-García, Carlos; García‐Ruiz, Cristina; Sánchez-Ruíz, Antonio; Pino‐González, M. Soledad; García‐Castro, Miguel; Chammaa, Samy

doi:10.1002/ejoc.201402221

Cited by 14 publications

(12 citation statements)

References 123 publications

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“…Sphingoid bases are key building blocks of sphingolipids, which play crucial structural and signaling functions . The biological importance of phytosphingosines and their difficult isolation have spurred wide interest in their chemical synthesis …”

mentioning

confidence: 91%

Chemo- and Diastereoselective N-Heterocyclic Carbene-Catalyzed Cross-Benzoin Reactions Using N-Boc-α-amino Aldehydes

Haghshenas

Gravel

2016

Org. Lett.

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N-Boc-α-amino aldehydes are shown to be excellent partners in cross-benzoin reactions with aliphatic or heteroaromatic aldehydes. The chemoselectivity of the reaction and the facial selectivity on the amino aldehyde allow cross-benzoin products to be obtained in good yields and good diastereomeric ratios. The developed method is utilized as the key step in a concise total synthesis of d-arabino-phytosphingosine.

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mentioning

confidence: 91%

Chemo- and Diastereoselective N-Heterocyclic Carbene-Catalyzed Cross-Benzoin Reactions Using N-Boc-α-amino Aldehydes

Haghshenas

Gravel

2016

Org. Lett.

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“…In 2014, Sarabia and co-workers demonstrated a sulfonium salt catalyzed asymmetric epoxidation protocol for the total synthesis of clavaminols. 35 As shown in Scheme 11, the chiral epoxy amide 57 was constructed stereoselectively from decanal (55) and sulfonium salt 56 36 under basic conditions. Treatment of 57 with ammonia led to the corresponding 2-amino-3-hydroxy amide 58, which was subjected to NH 3 •BH 3 /LDA to furnish deacetyl (+)-clavaminol H (5) in 45% overall yield.…”

Section: Total Synthesis By Sarabia and Colleagues (2014)mentioning

confidence: 99%

Recent Advances in the Total Synthesis of Clavaminols

et al. 2018

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Clavaminols are a new class of long-chain 2-amino-3-alkanols that mostly contain 2R,3S-configurations. Owing to their interesting molecular architectures and promising activities, they have become popular targets for synthetic organic chemists. In this review, we highlight 12 total syntheses of clavaminols from different research groups during the period 2009 to 2018.1 Introduction2 Synthetic Approaches toward Clavaminols2.1 Total Synthesis by Chemla and Colleagues (2009)2.2 Total Synthesis by Greck and Colleagues (2010)2.3 Total Synthesis by Sutherland and Zaed (2011)2.4 Total Synthesis by Huang and Colleagues (2011)2.5 Total Synthesis by Kotora and Colleagues (2012)2.6 Total Synthesis by Kumar and Colleagues (2013)2.7 Total Synthesis by Prabhavathi Devi and Colleagues (2013 and 2016)2.8 Total Synthesis by Sarabia and Colleagues (2014)2.9 Total Synthesis by Mohapatra and Colleagues (2016)2.10 Total Synthesis by Lu and Colleagues (2016)2.11 Total Synthesis by Jin and Colleagues (2017)2.12 Total Synthesis by Kumar Pandey and Colleagues (2018)3 Conclusion

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“…The versatility of this methodology was demonstrated in the total syntheses of bengamides analogues [128], a family of marine natural products isolated from sponges, exhibiting prominent antitumor, antihelmintic, and antibiotic activities as well as natural product (-)-depudecin [129], an antiangiogenic microbial polyketide (Scheme 57). Further applications include the synthesis of cyclodepsipeptides globomycin and SF-1902 A5 [130], and sphingoid-type bases [131].…”

Section: Asymmetric Sulfur Ylide-mediated Epoxidations As Key Stepsmentioning

confidence: 99%

Applications of Chiral Three-membered Rings for Total Synthesis: A Review

Dalpozzo¹,

Lattanzi

Pellissier

2017

COC

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This review updates recent applications of asymmetric aziridination, azirination, thiirination, epoxidation, and cyclopropanation in the total synthesis of biologically active compounds, including natural products, using chiral substrates or chiral catalysts, covering the literature since 2000. The interest towards these synthetic methodologies of chiral three-membered rings has increased in the last decade, dictated either by the biological activities that display many naturally occurring products bearing a three-membered unit or by the ring strain of three-membered rings making them useful precursors of many more complex interesting molecules. Classic as well as modern protocols in asymmetric aziridinations, azirinations, epoxidations, thiirinations, and cyclopropanations have been widely applied as key steps of a number of syntheses of important products. Although the use of chiral substrates and auxiliaries is still highly employed particularly in asymmetric aziridination and cyclopropanation, the development of enantioselective catalytic methodologies has witnessed exponential growth during the last decade. The present review is subdivided into three parts, dealing successively with the use of chiral nitrogen-containing three-membered rings, chiral epoxides and thiiranes, and chiral cyclopropanes in total synthesis.

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Exploring the Reactivity of Chiral Glycidic Amides for Their Applications in Synthesis of Bioactive Compounds

Cited by 14 publications

References 123 publications

Chemo- and Diastereoselective N-Heterocyclic Carbene-Catalyzed Cross-Benzoin Reactions Using N-Boc-α-amino Aldehydes

Chemo- and Diastereoselective N-Heterocyclic Carbene-Catalyzed Cross-Benzoin Reactions Using N-Boc-α-amino Aldehydes

Recent Advances in the Total Synthesis of Clavaminols

Applications of Chiral Three-membered Rings for Total Synthesis: A Review

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