Concise synthesis of the Taxol side chain and demethoxy-4-epi-cytoxazone via oxazoline formation through intramolecular benzylic substitution of a bis-trichloroacetimidate

Matsushima, Yoshitaka; Orita, Mina

doi:10.1016/j.tetlet.2021.153095

Cited by 6 publications

(2 citation statements)

References 65 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thus, various researchers have reported varied methodologies for its synthesis. Considering the vital importance of this moiety, Matsushima et al [ 140 ] in 2021 reported the total synthesis of the taxol side chain. This side chain can be synthesized from demethoxy-4-epi-cytoxazone, which is a naturally occurring compound isolated from Streptomyces species.…”

Section: Review Of the Literaturementioning

confidence: 99%

Sharpless Asymmetric Dihydroxylation: An Impressive Gadget for the Synthesis of Natural Products: A Review

et al. 2023

View full text Add to dashboard Cite

Sharpless asymmetric dihydroxylation is an important reaction in the enantioselective synthesis of chiral vicinal diols that involves the treatment of alkene with osmium tetroxide along with optically active quinine ligand. Sharpless introduced this methodology after considering the importance of enantioselectivity in the total synthesis of medicinally important compounds. Vicinal diols, produced as a result of this reaction, act as intermediates in the synthesis of different naturally occurring compounds. Hence, Sharpless asymmetric dihydroxylation plays an important role in synthetic organic chemistry due to its undeniable contribution to the synthesis of biologically active organic compounds. This review emphasizes the significance of Sharpless asymmetric dihydroxylation in the total synthesis of various natural products, published since 2020.

show abstract

Section: Review Of the Literaturementioning

confidence: 99%

Sharpless Asymmetric Dihydroxylation: An Impressive Gadget for the Synthesis of Natural Products: A Review

et al. 2023

View full text Add to dashboard Cite

show abstract

“…Chiral β-amino alcohols are widely present in pharmaceuticals, agrochemicals, and natural products (Figure a) . They also act as versatile ligands in asymmetric catalysis, facilitating the creation of complex chiral molecules with high selectivity and efficiency .…”

mentioning

confidence: 99%

Cr-Catalyzed Asymmetric Cross Aza-Pinacol Couplings for β-Amino Alcohol Synthesis

Hu,

Wang

2023

J. Am. Chem. Soc.

View full text Add to dashboard Cite

Chiral β-amino alcohols are crucial structural motifs found in pharmaceuticals, natural products, and chiral ligands in asymmetric catalysis. Despite previous advances, the development of catalytic approaches to access β-amino alcohols bearing vicinal stereocenters from readily available chemicals remains a prominent challenge. Herein, we describe the Cr-catalyzed asymmetric cross aza-pinacol coupling of aldehydes and N-sulfonyl imines. This protocol proceeds in a radical-polar crossover manner from the intermediacy of an α-amino radical instead of a ketyl radical. Key to the success is using a chiral chromium catalyst, which plays a triple role in the chemoselective single-electron reduction of the imine, fast radical interception to inhibit radical addition to imines, and chemo-and stereoselective addition to aldehydes instead of imines. This method provides a modular and efficient approach to accessing diverse β-amino alcohols bearing vicinal stereocenters.

show abstract

Gram-scale synthesis of cytoxazone via dihydrooxazine formation through SiO2-promoted intramolecular substitution of a trichloroacetimidate

Matsushima,

Otsuka,

Ishikawa

et al. 2023

Tetrahedron Letters

View full text Add to dashboard Cite

Concise synthesis of the Taxol side chain and demethoxy-4-epi-cytoxazone via oxazoline formation through intramolecular benzylic substitution of a bis-trichloroacetimidate

Cited by 6 publications

References 65 publications

Sharpless Asymmetric Dihydroxylation: An Impressive Gadget for the Synthesis of Natural Products: A Review

Sharpless Asymmetric Dihydroxylation: An Impressive Gadget for the Synthesis of Natural Products: A Review

Cr-Catalyzed Asymmetric Cross Aza-Pinacol Couplings for β-Amino Alcohol Synthesis

Gram-scale synthesis of cytoxazone via dihydrooxazine formation through SiO2-promoted intramolecular substitution of a trichloroacetimidate

Contact Info

Product

Resources

About