Novel protection of 1,2-diol for trans-dihydroxycyclopentene ring construction by the C H insertion of alkylidene carbene: Formal total synthesis of (+)-trehazolin

Ohira, Susumu; Kuboki, Atsuhito; Takimoto, Yoshimi; Matsuda, Kyosuke; Itasaki, Saori; Urushibata, Yuki; Takano, Y.; Nakamura, Y.

doi:10.1016/j.tetlet.2019.151085

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Cited by 2 publications

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“…In a second route [43] to trehazolin 2.22 (Scheme 31), Ohira and coworkers introduced an alternative diol protecting group. Cyclization of 6.8 with TMSCHN 2 proceeded smoothly to give 6.9 .…”

Section: Recent Developmentsmentioning

confidence: 99%

Natural Product Synthesis by Intramolecular Alkylidene Carbene C−H Insertion

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2022

Eur J Org Chem

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Section: Recent Developmentsmentioning

confidence: 99%

Natural Product Synthesis by Intramolecular Alkylidene Carbene C−H Insertion

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2022

Eur J Org Chem

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Direct Access to Monoprotected Homoallylic 1,2-Diols via Dual Chromium/Photoredox Catalysis

et al. 2020

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Herein, we present a dual catalytic strategy to efficiently obtain mono-protected homoallylic 1,2-diols by coupling abundant aldehydes with simple (silyl) enol ethers, thus providing direct access to this important motif without the (super)stoichiometric use of prefunctionalized metal-allyl species. The modularity of our approach is shown by the introduction of several silyl-and alkyl-based protecting groups, enabling a diverse protecting group strategy. To highlight functional group tolerance and chemoselectivity, we demonstrate the functionalization of a variety of aliphatic, aromatic and heteroaromatic aldehydes, even in presence of ketones and esters. The applicability was further supported by a large scale experiment and a robustness screening. Mechanistic studies support a radical mechanism, starting from the single electron oxidation of the silyl enol ether, facilitated by the β-silicon effect.

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Novel protection of 1,2-diol for trans-dihydroxycyclopentene ring construction by the C H insertion of alkylidene carbene: Formal total synthesis of (+)-trehazolin

Cited by 2 publications

References 24 publications

Natural Product Synthesis by Intramolecular Alkylidene Carbene C−H Insertion

Natural Product Synthesis by Intramolecular Alkylidene Carbene C−H Insertion

Direct Access to Monoprotected Homoallylic 1,2-Diols via Dual Chromium/Photoredox Catalysis

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