1,2-Anti aldol methodologies used in natural product synthesis

Thanh, Nhan Do Van

doi:10.1016/j.tet.2019.130618

Scalable Total Synthesis of Acremolactone B

Ba,

He,

Ren

et al. 2024

Angewandte Chemie

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Acremolactone B is a pyridine‐containing azaphilone‐type polyketide with herbicidal activity. We developed an aza‐6π electrocyclization−aromatization strategy to construct the tetrasubstituted pyridine ring and achieved the first total synthesis of this molecule on a gram scale. A bicyclic intermediate was expeditiously prepared by using [2 + 2] photocycloaddition and chemoselective Baeyer−Villiger oxidation, which was further elaborated to a densely substituted aza‐triene. An electrocyclization−aromatization cascade was exploited to forge the tetracyclic core of the natural product, and the side chain was introduced through diastereoselective acylation and reduction.

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Scalable Total Synthesis of Acremolactone B

Ba,

He,

Ren

et al. 2024

View full text Add to dashboard Cite

Acremolactone B is a pyridine‐containing azaphilone‐type polyketide with herbicidal activity. We developed an aza‐6π electrocyclization−aromatization strategy to construct the tetrasubstituted pyridine ring and achieved the first total synthesis of this molecule on a gram scale. A bicyclic intermediate was expeditiously prepared by using [2 + 2] photocycloaddition and chemoselective Baeyer−Villiger oxidation, which was further elaborated to a densely substituted aza‐triene. An electrocyclization−aromatization cascade was exploited to forge the tetracyclic core of the natural product, and the side chain was introduced through diastereoselective acylation and reduction.

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Carbonylchemie

Düfert¹

2023

Organische Synthesemethoden

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1,2-Anti aldol methodologies used in natural product synthesis

Cited by 6 publications

References 123 publications

Scalable Total Synthesis of Acremolactone B

Scalable Total Synthesis of Acremolactone B

Scalable Total Synthesis of Acremolactone B

Carbonylchemie

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