Synthesis of tubuvaline (Tuv) fragment of tubulysin via diastereoselective dihydroxylation of homoallylamine

Reddy, Ramesh B.; Vijay, M.; Krishnan, Mena Asha; Chelvam, Venkatesh

doi:10.1080/00397911.2020.1855355

Cited by 2 publications

(1 citation statement)

References 35 publications

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“…Tubulysins consist of four amino acid chains, i.e., one naturally occurring isoleucine and three other unofficial amino acids. One of them is tubuvaline (Tuv), whose facile synthesis was recently reported by Reddy et al [ 91 ] in 2021. The key steps of this synthesis are Sharpless asymmetric dihydroxylation and aziridine ring opening reaction.…”

Section: Review Of the Literaturementioning

confidence: 99%

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

et al. 2023

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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.

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Section: Review Of the Literaturementioning

confidence: 99%

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

et al. 2023

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The Recent Developments of ADCs with the Tubulysins as the Payloads

Yao

2023

MRMC

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As a novel bio-targeting antitumor agent, an antibody-drug conjugate (ADC) combines the high selectivity of monoclonal antibody and potent cytotoxicity of drug or payload. It can expand the scope of clinical application of small molecule drugs. Tubulysin and its bio-precursor pretubulysin (PT) are potent tubulin-binding antitumor drugs. Due to the excellent antitumoral, antimetastatic, antiangiogenic, and anti-multidrug resistance properties, Tubulysins or PT is believed to be a promising cancer therapeutic approach. Currently, the modifications of tubulysin are centering on the C-11 acetoxyl and N,O-acetal groups, and numerous promising payloads are identified. There are at least 5 sites to introduce appropriate drug linkers in tubulysin and PT for connecting the antibodies. The possible sites of attachment are located in Mep, Tuv, or Tup parts. Cleavage and non-cleavage linkers are used in these ADCs. The chemical reactions involved in the final conjugation of antibody and linker-payload (LP) are cysteine, lysine, site-specific, and click chemistry reactions. In this article, the recent development of ADCs with tubulysins as the payloads is reviewed, with the hope of providing a reference and future strategies for developing new ADSs.

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Synthesis of tubuvaline (Tuv) fragment of tubulysin via diastereoselective dihydroxylation of homoallylamine

Cited by 2 publications

References 35 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

The Recent Developments of ADCs with the Tubulysins as the Payloads

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