2019
DOI: 10.1002/ange.201906158
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Asymmetric Total Synthesis of (+)‐Neooxazolomycin Using a Chirality‐Transfer Strategy

Abstract: The total synthesis of (+ +)-neooxazolomycin was achieved from the amino-acid d-serine.T he efficiency of this approach is derived from the use of principles of memory of chirality and dynamic kinetic resolution in the intramolecular aldol reaction of as erine derivative to build the densely functionalizedl actam framework and to install three contiguous stereocenters.T he key intermediate was readily elaborated to the target natural product.Supportinginformation and the ORCID identification number(s) for the … Show more

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Cited by 20 publications
(6 citation statements)
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“… , As expected, comparatively fewer examples of structurally characterized N-pyramidalized amides embedded in six-membered rings have been reported; however, these amides feature significant N-pyramidalization (average χ N of 46.1°), while twist is much lower (average τ of 11.2°). These values compare well with the five-membered fused ring lactams (χ N , 45.9°; τ, 11.7°), , …”
Section: Cyclic Amides: N-pyramidalization 40–60°supporting
confidence: 71%
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“… , As expected, comparatively fewer examples of structurally characterized N-pyramidalized amides embedded in six-membered rings have been reported; however, these amides feature significant N-pyramidalization (average χ N of 46.1°), while twist is much lower (average τ of 11.2°). These values compare well with the five-membered fused ring lactams (χ N , 45.9°; τ, 11.7°), , …”
Section: Cyclic Amides: N-pyramidalization 40–60°supporting
confidence: 71%
“…Similar to β-lactams, the amide bond geometry of structurally characterized amides embedded in a fused five-membered ring system (Figures –) , can be characterized as N-pyramidalized (average χ N of 45.9°) with minimal twist (average τ of 11.7°). As expected, the average values of N-pyramidalization and twist are slightly lower as compared to β-lactams ...…”
Section: Cyclic Amides: N-pyramidalization 40–60°mentioning
confidence: 99%
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“…[16][17][18] The unique structure and multiple biological activities of oxazolomycins has attracted much attention from organic chemists. The total synthesis of neooxazolomycin, 19,20 oxazolomycin A, 21 and lajollamycin 22 has been accomplished. In addition, several synthesis method to establish the different structural segments of oxazolomycins have been reported.…”
Section: Introductionmentioning
confidence: 99%