Total Synthesis of Trioxacarcins DC-45-A1, A, D, C, and C7″-<i>epi</i>-C and Full Structural Assignment of Trioxacarcin C

Nicolaou, K. C.; Cai, Quan; Sun, Hongbao; Qin, Bo; Zhu, Shugao

doi:10.1021/jacs.5b12687

Cited by 41 publications

(23 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Extensive mechanistic studies have been performed on the reaction, which supports a mechanism shown in Scheme . The utility of this protocol has been demonstrated by its applications in the total syntheses of natural products including periploside A, acremomannolipin A, and trioxacarcins …”

Section: Transition Metal Catalysismentioning

confidence: 62%

Recent Developments in Stereoselective Chemical Glycosylation

Ling

Bennett

2019

Asian J Org Chem

View full text Add to dashboard Cite

Because of their pivotal biological functions, attention to sugars and glycobiology has grown rapidly in recent decades, leading to increased demand for homogeneous oligosaccharides. The stereoselective preparation of oligosaccharides by chemical means remains challenging and continues to be a vivid research area for organic chemists. In the past decade, new approaches and reinvestigated tradi-tional methods have transformed the field. These developments include novel catalyses, various types of glycosylation modulators and the use of photochemical energy to facilitate glycosylation. This Minireview presents a brief overview of the latest trends in chemical glycosylation, with emphasis on the stereoselective synthetic protocols developed in the past decade.[a] Dr.

show abstract

Section: Transition Metal Catalysismentioning

confidence: 62%

Recent Developments in Stereoselective Chemical Glycosylation

Ling

Bennett

2019

Asian J Org Chem

View full text Add to dashboard Cite

show abstract

“…Next, we screened various Lewis or Brønsted acids to install the bridged acetal group via a ring opening/acetalation process. We found that SnCl 4 59 , 60 smoothly catalyzed this tandem process and led to the formation of 95 in 85% yield. Subsequent CAN oxidation afforded oncocalyxone B ( 6 ) in 92% yield; 1 H and 13 C nuclear magnetic resonance (NMR) spectra and high-resolution mass spectrometry data for this synthetic compound were fully consistent with those of the natural product 14 , 15 .…”

Section: Resultsmentioning

confidence: 87%

Ti(Oi-Pr)4-promoted photoenolization Diels–Alder reaction to construct polycyclic rings and its synthetic applications

et al. 2017

View full text Add to dashboard Cite

Stereoselective construction of polycyclic rings with all-carbon quaternary centers, and vicinal all-carbon quaternary stereocenters, remains a significant challenge in organic synthesis. These structures can be found in a wide range of polycyclic natural products and drug molecules. Here we report a Ti(Oi-Pr)4-promoted photoenolization/Diels–Alder (PEDA) reaction to construct hydroanthracenol and related polycyclic rings bearing all-carbon quaternary centers. This photolysis proceeds under mild conditions and generates a variety of photo-cycloaddition products in good reaction efficiency and stereoselectivity (48 examples), and has been successfully used in the construction of core skeleton of oncocalyxones, tetracycline and pleurotin. It also provides a reliable method for the late-stage modification of natural products bearing enone groups, such as steroids. The total synthesis of oncocalyxone B was successfully achieved using this PEDA approach.

show abstract

“…Between 2015 and 2017, the Nicolaou group [89,90,91] developed the elegant divergent total synthesis of five highly potent cytotoxic agents trioxacarcins DC-45-A1, DC-45-A2, A, C, and D from a common trioxacarcin precursor 119 , which was efficiently constructed using asymmetric organocatalytic epoxidation as one of the most versatile strategies (Scheme 32).…”

Section: Asymmetric Total Synthesis Of Bioactive Natural Products mentioning

confidence: 99%

Advances in the Asymmetric Total Synthesis of Natural Products Using Chiral Secondary Amine Catalyzed Reactions of α,β-Unsaturated Aldehydes

Wang

2019

Molecules

View full text Add to dashboard Cite

Chirality is one of the most important attributes for its presence in a vast majority of bioactive natural products and pharmaceuticals. Asymmetric organocatalysis methods have emerged as a powerful methodology for the construction of highly enantioenriched structural skeletons of the target molecules. Due to their extensive application of organocatalysis in the total synthesis of bioactive molecules and some of them have been used in the industrial synthesis of drugs have attracted increasing interests from chemists. Among the chiral organocatalysts, chiral secondary amines (MacMillan’s catalyst and Jorgensen’s catalyst) have been especially considered attractive strategies because of their impressive efficiency. Herein, we outline advances in the asymmetric total synthesis of natural products and relevant drugs by using the strategy of chiral secondary amine catalyzed reactions of α,β-unsaturated aldehydes in the last eighteen years.

show abstract

Total Synthesis of Trioxacarcins DC-45-A1, A, D, C, and C7″-epi-C and Full Structural Assignment of Trioxacarcin C

Cited by 41 publications

References 32 publications

Recent Developments in Stereoselective Chemical Glycosylation

Recent Developments in Stereoselective Chemical Glycosylation

Ti(Oi-Pr)4-promoted photoenolization Diels–Alder reaction to construct polycyclic rings and its synthetic applications

Advances in the Asymmetric Total Synthesis of Natural Products Using Chiral Secondary Amine Catalyzed Reactions of α,β-Unsaturated Aldehydes

Contact Info

Product

Resources

About