Short synthesis of epi-cytoxazone via oxazoline formation through intramolecular benzylic substitution of a bis-trichloroacetimidate

Matsushima, Yoshitaka; Ishikawa, Moe; Shibasaki, Rina; Nojima, Yuki

doi:10.1016/j.tetlet.2017.11.057

Cited by 6 publications

(2 citation statements)

References 40 publications

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“…Some interesting examples are given in racemic and enantioselective synthesis studies. [11][12][13][14][15][16] Lu et al 12 developed a new protocol for the synthesis of (±)-epi-cytoxazone that consists of a cascade of organocatalytic reactions between a sulfur ylide and a Smitha and Reddy 13 synthesized (+)-epi-cytoxazone in six steps, starting from anisaldehyde and using Sharpless kinetic resolution followed by Mitsunobu inversion to obtain the target molecule with the desired stereochemistry.…”

Section: Introductionmentioning

confidence: 99%

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New Approach for the Stereoselective Synthesis of (+)-epi-Cytoxazone

Miranda¹,

Sartori²,

Diaz³

et al. 2018

J. Braz. Chem. Soc.

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The stereoselective total synthesis of (+)-epi-cytoxazone was performed satisfactorily in 8 steps, in 17% overall yield, via a novel route from 2,3-O-(3-pentylidene)-(R)-glyceraldehyde. The bulky group alkene-ketal allowed intramolecular control of the target molecule's asymmetric centers in the dihydroxylation step by promoting the approach of OsO 4 to the face opposite to that of the ketal group.

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Section: Introductionmentioning

confidence: 99%

“…In a recent publication, Matsushima et al 16 reported the synthesis of (−)-epi-cytoxazone through an oxazoline intermediate, whose formation was based on the intramolecular benzylic substitution of 1,2-bis-trichloroacetimidate obtained from the respective enantiomerically pure diol.…”

Section: Introductionmentioning

confidence: 99%