Total Syntheses of Amphidinolides T1, T3, and T4

Clark, J. Stephen; Romiti, Filippo

doi:10.1002/anie.201305467

Cited by 23 publications

(13 citation statements)

References 70 publications

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“…This type of transformation found use in the synthesis of amphidinolides T1, T3, and T4, 75 a highly studied class of macrolides of marine origin. 94 In their approach, Clark and Romiti treated alkyne 67 with (EtO) 3 SiH in the presence of the usual [Cp*Ru(MeCN) 3 ]PF 6 catalyst to obtain an equimolar Elaboration into the corresponding α-hydroxy ketones involved a stereoselective epoxidation under Shi conditions 95 followed by TamaoFleming oxidation 3335 of the resulting epoxy silanes.…”

mentioning

confidence: 99%

Progress in the trans-Reduction and trans-Hydrometalation of Internal Alkynes. Applications to Natural Product Synthesis

Frihed

Fürstner

2016

Bulletin of the Chemical Society of Japan

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The classical repertoire of synthetic organic chemistry is short of methods that allow triple bonds to be transformed into (E)-alkenes with high selectivity in the presence of other reducible sites. Recent advances, most notably in ruthenium-catalyzed trans-hydrogenation, trans-hydrosilylation, trans-hydrogermylation, trans-hydrostannation, and even trans-hydroboration hold the promise of filling this gap. This review illustrates the state-of-the-art in the field by summarizing applications of these emerging methodologies to natural product synthesis. A comparison of ruthenium-catalyzed and radical-induced trans-hydrostannations provides further insights into the application profile of these transformations

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confidence: 99%

Progress in the trans-Reduction and trans-Hydrometalation of Internal Alkynes. Applications to Natural Product Synthesis

Frihed

Fürstner

2016

Bulletin of the Chemical Society of Japan

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“…One such application is elegantly illustrated with the total syntheses of amphidinolides T1, T3, and T4 by Clark and Romiti (Scheme 26). 146 As for amphidinolide V, discussed above, the amphidinolides T1, T3, and T4 are also macro-lides isolated from marine dinoflagellates with potent cytotoxic activities. Structurally, the so-named amphidinolides of the T series are characterized by the presence of a trisubstituted tetrahydrofuran.…”

Section: Scheme 25 Total Synthesis Of Epothilone Bmentioning

confidence: 98%

Recent Advances in Total Synthesis via Metathesis Reactions

Cheng-Sánchez

Sarabia

2018

Synthesis

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The metathesis reactions, in their various versions, have become a powerful and extremely valuable tool for the formation of carbon–carbon bonds in organic synthesis. The plethora of available catalysts to perform these reactions, combined with the various transformations that can be accomplished, have positioned the metathesis processes as one of the most important reactions of this century. In this review, we highlight the most relevant synthetic contributions published between 2012 and early 2018 in the field of total synthesis, reflecting the state of the art of this chemistry and demonstrating the significant synthetic potential of these methodologies.1 Introduction2 Alkene Metathesis in Total Synthesis2.1 Total Synthesis Based on a Ring-Closing-Metathesis Reaction2.2 Total Synthesis Based on a Cross-Metathesis Reaction2.3 Strategies for Selective and Efficient Metathesis Reactions of Alkenes2.3.1 Temporary Tethered Ring-Closing Metathesis2.3.2 Relay Ring-Closing Metathesis2.3.3 Stereoselective Alkene Metathesis2.3.4 Alkene Metathesis in Tandem Reactions3 Enyne Metathesis in Total Synthesis3.1 Total Syntheses Based on a Ring-Closing Enyne-Metathesis Reaction3.2 Total Syntheses Based on an Enyne Cross-Metathesis Reaction3.3 Enyne Metathesis in Tandem Reactions4 Alkyne Metathesis in Total Synthesis4.1 Total Synthesis Based on a Ring-Closing Alkyne-Metathesis Reaction4.2 Other Types of Alkyne-Metathesis Reactions5 Conclusions

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“…Structurally, amphidinolides of the T series vary only in their oxygenation motif and stereochemistry in the C12-C14 area, and amphidinolide T1is the isomer of T3-T5. [113] The efficient and high-yielding total syntheses of natural products amphidinolides T1 (58), T3 (59), and T4 (60) were achieved by Romiti and co-workers involving macrolactonization using Yamaguchi method as a crucial step in 2013. [113] The starting material the commercially available alcohol (55) was effective to provide seco acid (56) in high yield (86 %).…”

Section: Total Syntheses Of Amphidinolides T1 T3 and T4mentioning

confidence: 99%

“…[113] The efficient and high-yielding total syntheses of natural products amphidinolides T1 (58), T3 (59), and T4 (60) were achieved by Romiti and co-workers involving macrolactonization using Yamaguchi method as a crucial step in 2013. [113] The starting material the commercially available alcohol (55) was effective to provide seco acid (56) in high yield (86 %). Next, macrolactonization of seco acid (56) took place to furnish key intermediate (57) in the presence of the TCBC and DMAP in toluene at room temperature to 45 0 C under Yamaguchi conditions in 80 % yield (Scheme 19).…”

Section: Total Syntheses Of Amphidinolides T1 T3 and T4mentioning

confidence: 99%

Applications of Yamaguchi Method to Esterification and Macrolactonization in Total Synthesis of Bioactive Natural Products

Majhi

2021

ChemistrySelect

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Yamaguchi protocol provides functionalized esters regioselectively from carboxylic acids and alcohols employing 2,4,6trichlorobenzoyl chloride as the condensation reagent in the presence of a stoichiometric amount of 4-N,N-dimethylaminopyridine. The key features of this method comprise a high yield of esters, short reaction time, mild conditions, macrocyclic lactone ring formation, and regioselective preparation of highly functionalized esters. Such beneficial quality of this method as a whole have motivated the organic chemist and biological community to explore the application of Yamaguchi protocol in more heights and as a result, the present overview is aimed to cover the application of this method as a key step in the area of the total synthesis of bioactive natural products. The present review tries to focus on the natural sources, structures, and biological activities of the promising natural products elegantly.

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Total Syntheses of Amphidinolides T1, T3, and T4

Cited by 23 publications

References 70 publications

Progress in the trans-Reduction and trans-Hydrometalation of Internal Alkynes. Applications to Natural Product Synthesis

Progress in the trans-Reduction and trans-Hydrometalation of Internal Alkynes. Applications to Natural Product Synthesis

Recent Advances in Total Synthesis via Metathesis Reactions

Applications of Yamaguchi Method to Esterification and Macrolactonization in Total Synthesis of Bioactive Natural Products

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