Asymmetric Total Synthesis of (−)-4-Hydroxyzinowol, a Highly Oxygenated Dihydro-β-Agarofuran

Urabe, Daisuke; Todoroki, Hidenori; Inoue, M.

doi:10.5059/yukigoseikyokaishi.73.1081

Cited by 2 publications

(1 citation statement)

References 88 publications

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“…Another example of the Trost oxidation as a key late-stage step is Inoue and coworkers' total synthesis of (À )-4hydroxyzinowol, a highly oxygenated tricyclic natural product with potent inhibitory activity against the multi-drug resistance transporter P-glycoprotein (P-gp). [16] In this key step, the secondary alcohol of the heavily oxygenated intermediate 24 was successfully oxidized in the presence of a primary alcohol, a tertiary alcohol, and two TBS-protected secondary alcohols (Scheme 4). Following oxidation, the primary alcohol cyclized onto the resulting ketone to yield hemiketal 25.…”

Section: Oxidations Of Alcohols and Aldehydesmentioning

confidence: 99%

Beyond Allylic Alkylation: Applications of Trost Chemistry in Complex Molecule Synthesis

Tracy

Kalnmals

Toste

2021

Israel Journal of Chemistry

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During his fifty-five year tenure, Prof. Barry M. Trost has made countless advancements in the fields of synthetic method development and complex molecule total synthesis. In addition to his well-known contributions in the areas of allylic alkylation and transition metal-catalyzed cycloisomerization reactions, Prof. Trost has developed many other useful synthetic methods as well. Although less prominent than some of his hallmark transformations, these reactions are no less significant and have enjoyed widespread adoption by the synthetic community. This review highlights many of these unsung processes -including several reduction/oxidation reactions, metal-catalyzed alkene-alkyne and alkyne-alkyne couplings, phosphine-catalyzed redox isomerizations, and methods for determining absolute stereochemistry -and their utility in the total synthesis of natural products, pharmaceuticals, and other complex bioactive molecules.

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Section: Oxidations Of Alcohols and Aldehydesmentioning

confidence: 99%

Beyond Allylic Alkylation: Applications of Trost Chemistry in Complex Molecule Synthesis

Tracy

Kalnmals

Toste

2021

Israel Journal of Chemistry

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Enantioselective, Rhodium‐Catalyzed 1,4‐Addition of Organoboron Reagents to Electron‐Deficient Alkenes

2017

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The rhodium‐catalyzed 1,4‐addition of organoboron reagents to electron‐deficient alkenes is a versatile method for the enantioselective construction of carbon–carbon bonds. The scope of these reactions is broad, and alkenes activated by adjacent carbonyls, imines, nitriles, phosphonyl groups, nitro groups, sulfonyl groups, C=N‐containing aromatic heterocycles, electron‐deficient arenes, or boryl groups are effective substrates. Regarding the pronucleophilic component, aryl‐, heteroaryl‐, and alkenylboron reagents have been successfully employed. In addition, numerous chiral ligands have been developed which impart high enantioselectivities onto these reactions. Importantly, these reactions usually proceed under mild, experimentally convenient conditions, with no requirement for precautions to exclude air or moisture. This chapter presents the scope and limitations of this process, along with a discussion of the current understanding of the mechanistic and stereochemical features. Incorporation of this process into domino reactions is discussed, as is its application in the synthesis of biologically active molecules. The literature is covered up until the end of 2013.

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Asymmetric Total Synthesis of (−)-4-Hydroxyzinowol, a Highly Oxygenated Dihydro-β-Agarofuran

Cited by 2 publications

References 88 publications

Beyond Allylic Alkylation: Applications of Trost Chemistry in Complex Molecule Synthesis

Beyond Allylic Alkylation: Applications of Trost Chemistry in Complex Molecule Synthesis

Enantioselective, Rhodium‐Catalyzed 1,4‐Addition of Organoboron Reagents to Electron‐Deficient Alkenes

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