Total Synthesis of (−)-Enigmazole A

@article{Ai2015TotalSO,
  title={Total Synthesis of (−)-Enigmazole A},
  author={Yanran Ai and Mariya V. Kozytska and Yike Zou and Anton S. Khartulyari and Amos B. Smith},
  journal={Journal of the American Chemical Society},
  year={2015},
  volume={137},
  pages={15426 - 15429}
}
A highly convergent, stereocontrolled total synthesis of the architecturally complex marine sponge metabolite (−)-enigmazole A has been achieved. Highlights include an unprecedented late-stage large-fragment Petasis–Ferrier union/rearrangement, a multicomponent Type I Anion Relay Chemistry (ARC) tactic, and a dithiane–epoxide union in conjunction with an oxazole-directed stereoselective reduction. 
24 Citations
Total Synthesis of (-)-Enigmazole A.
TLDR
Total synthesis of (-)-enigmazole A, a marine macrolide natural product with cytotoxic activity, has been accomplished through gold-catalyzed rearrangement of a propargylic benzoate and ring-closing metathesis of the resultant α,β-unsaturated ketone.
Total Synthesis of the Marine Phosphomacrolide, (-)-Enigmazole A, Exploiting Multicomponent Type I Anion Relay Chemistry (ARC) in Conjunction with a Late-Stage Petasis-Ferrier Union/Rearrangement.
An effective late-stage large-fragment union/rearrangement exploiting the Petasis-Ferrier protocol, in conjunction with multicomponent Type I Anion Relay Chemistry (ARC) to access advanced
Unified Total Synthesis of (-)-Enigmazole A and (-)-15-O-Methylenigmazole A.
TLDR
Late-stage diversification of a common intermediate enabled unified total synthesis of (-)-enigmazole A and (-)-15- O -methylenigmZole A, cytotoxic marine phosphomacrolides.
Total Synthesis of (−)-Mandelalide A Exploiting Anion Relay Chemistry (ARC): Identification of a Type II ARC/CuCN Cross-Coupling Protocol
TLDR
The synthesis of marine macrolide A showcases ARC as a rapid, scalable coupling strategy for the union of simple readily available building blocks to access diverse complex molecular fragments with excellent stereochemical control.
Total Synthesis of Reported Structure of Baulamycin A and Its Congeners.
TLDR
This synthetic study disclosed that the reported structure of baulamycin A needs to be revised, as its spectroscopic data are not identical with those of the synthetic baulamicin A.
1,3-Bifunctional Nucleophilic Allylation Reagents: Preparative Methods and Synthetic Applications
TLDR
This short review of preparation methods of 1,3-Bifunctional nucleophilic allylation reagents and their reactions with various electrophiles concludes that these reagents play an important role in organic synthesis.
1,3-Dithianes as Acyl Anion Equivalents in Pd-Catalyzed Asymmetric Allylic Substitution.
TLDR
This work provides an alternative strategy utilizing electrophilic carbonyl compounds as nucleophilic species in a Pd-catalyzed allylic substitution with 1,3-dithianes as acyl anion equivalents, and the corresponding alkylated products were conveniently converted into several biologically active products.
Generation of Dithianyl and Dioxolanyl Radicals Using Photoredox Catalysis: Application in the Total Synthesis of the Danshenspiroketallactones via Radical Relay Chemistry.
TLDR
Visible-light-induced generation of dithianyl and dioxolanyl radicals via selective hydrogen atom transfer (HAT) has been achieved and the conformational stability of the danshenspiroketallactones has been defined via experiments and DFT calculations.
Merging Asymmetric [1,2]-Additions of Lithium Acetylides to Carbonyls with Type II Anion Relay Chemistry.
An enantioselective three-component coupling reaction has been developed, enabling the union of a variety of lithium acetylides and electrophiles exploiting an achiral linchpin via an anionic
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