Total Synthesis of (−)-Teucvidin

Liu, Xiaozu; Lee, Chi‐Sing

doi:10.1021/ol301098s

Cited by 35 publications

(20 citation statements)

References 35 publications

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“…This was subsequently transformed into (-)-teucvidin (220) via a short, high-yielding reaction sequence (Scheme 55). 79 Scheme 55 Synthesis of (-)-teucvidin…”

Section: Scheme 49 Formal Synthesis Of Palmerolide Amentioning

confidence: 99%

Furan Oxidation Reactions in the Total Synthesis of Natural Products

2018

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Recent developments on the transformations of furans under oxidative conditions toward the total synthesis of complex natural compounds are discussed. Reactions and methods are classified according to the type of oxidant used. Comparisons are then made between all the strategies to provide a comprehensive overview. This review covers the most prominent work published from 2011 until 2017.1 Introduction2 Reagents and Methods for Oxidation of the Furan Ring2.1 Singlet Oxygen2.2 Peroxides and Hydroperoxides2.3 Quinones2.4 Halogen-Based Oxidants2.5 Chromium-Based Oxidants3 The Achmatowicz Reaction3.1 Halogen-Based Oxidants3.2 Hydroperoxides3.3 Enzymatic Oxidation4 Conclusion

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“…This was subsequently transformed into (-)-teucvidin (220) via a short, high-yielding reaction sequence (Scheme 55). 79 Scheme 55 Synthesis of (-)-teucvidin…”

Section: Scheme 49 Formal Synthesis Of Palmerolide Amentioning

confidence: 99%

Furan Oxidation Reactions in the Total Synthesis of Natural Products

2018

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“…34 An asymmetric Michael/Conia-ene cascade cyclization, which utilizes substrate-control and takes advantage of the six-membered chair-like nature of the transition state in the Michael reaction, has been developed. As shown in Scheme 7, the chiral substrate 44 35 undergoes a highly diastereoselective intramolecular Michael reaction to form 45 upon treatment with Zn(OTf) 2 /Et 2 NH. This observation is in accord with a prediction based on of the more favorable chair-like transition state TS2.…”

Section: Account Syn Lettmentioning

confidence: 99%

Syntheses of Diverse Natural Products via Dual-Mode Lewis Acid Induced Cascade Cyclization Reactions

Du¹,

Wang²,

Ma³

et al. 2017

Synlett

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The σ/π-binding properties of a series of Lewis acids was studied using DFT calculations. The results led to the identification of Zn(II)/In(III) as a suitable dual-mode Lewis acid for use in promoting cascade cyclization reactions. Based on this finding, we developed three new types of dual-mode Lewis acid induced cascade cyclization reactions and have demonstrated the utilities of each process in natural product synthesis.1 Introduction2 Dual-Mode Lewis Acids3 Prins/Conia-Ene Cascade Reaction and its Applications4 Diels–Alder/Carbocyclization Cascade Reaction and Applications4.1 First Generation Diels–Alder/Carbocyclization Cascade Reaction and its Application4.2 Second Generation Diels–Alder/Carbocyclization Cascade Reaction and its Applications5 Michael/Conia-Ene Cascade Reaction and its Applications6 Conclusion

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“…Basic reaction conditions were successfully applied by Liu and Bittman in a linear allylic acetoxylation of a terminal alkene during the synthesis of a C-glycoside analogue of α-galactosylceramide (Scheme 24). [41] Under the acidic conditions first developed by White, [32a] a lower yield of allylic acetoxylation was achieved.…”

Section: Acetoxylations Hydroxylationsmentioning

confidence: 99%

Direct Allylic Functionalization Through Pd‐Catalyzed C–H Activation

et al. 2014

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After a brief introduction emphasizing the synthetic relevance of the allylic C–H activation step, evoking the first pioneering stoichiometric studies that sowed the “seeds” of this subject, and analyzing similarities and differences between a “classical” and a “direct” Pd‐catalyzed allylation process, this review outlines some selected examples of palladium‐catalyzed direct allylic functionalization. This old reaction, ignored for many years, is now living a new and exciting era.

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Total Synthesis of (−)-Teucvidin

Cited by 35 publications

References 35 publications

Furan Oxidation Reactions in the Total Synthesis of Natural Products

Furan Oxidation Reactions in the Total Synthesis of Natural Products

Syntheses of Diverse Natural Products via Dual-Mode Lewis Acid Induced Cascade Cyclization Reactions

Direct Allylic Functionalization Through Pd‐Catalyzed C–H Activation

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