Synthesis of the non-adjacent bis(tetrahydrofuran) core of squamostanin C by silicon-tethered, size-selective triple ring-closing metathesis

Quinn, Kevin J.; Hu, Yun; Miller, Patrick J. O.; Walsh, Ryan T.; Caporello, Michaella A.; Maliszewski, Mary L.; Markowski, Justin H.

doi:10.1016/j.tetlet.2019.05.064

Cited by 3 publications

(4 citation statements)

References 39 publications

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“…Compound 7 was purchased and used without further purification. 4-(Benzyloxy)butan-1-ol, 45 4-((tert-butyldiphenylsilyl)oxy)benzoic acid (22), 26 and hex-1-en-3-ol (25) 43 were synthesized following the cited literature procedures.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…The metathesis step then becomes a ring closing metathesis (RCM) reaction. Traceless removal of the tether after the RCM reaction, e.g., by hydrolysis, furnishes acyclic Z -alkenes that cannot be obtained by standard CM reactions. , In our tethered RCM variant, cleavage of the tether is accomplished by a base-induced elimination of the RCM products 2 that generates an additional E -configured double bond conjugated to a Z -double bond. A further difference as compared to other tethered RCM reactions is that the tether is retained in the product as a valuable carboxylate group.…”

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confidence: 99%

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Stereoselective Synthesis of Conjugated Polyenes Based on Tethered Olefin Metathesis and Carbonyl Olefination: Application to the Total Synthesis of (+)-Bretonin B

Lood

Schmidt

2020

J. Org. Chem.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

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confidence: 99%

Stereoselective Synthesis of Conjugated Polyenes Based on Tethered Olefin Metathesis and Carbonyl Olefination: Application to the Total Synthesis of (+)-Bretonin B

Lood

Schmidt

2020

J. Org. Chem.

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“…On the other hand, Quinnand's group revealed the synthesis of squamostanin C non‐adjacent bis ‐(tetrahydrofuran) core 998 (Scheme 156). Squamostanin C is a polyketide acetogenin isolated from Annonaceae plant species, generally Annonaceous acetogenins possess multiple biological activities and most of them are poweful cytotoxics [338a] . In this approach, TST‐RCM was used as one of the pivotal steps to give the compound 997 .…”

Section: Various Strategies/tactics In Olefin Metathesis Reactionsmentioning

confidence: 99%

Metathesis Reactions in Natural Product Fragments and Total Syntheses

et al. 2022

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The passion of total‐ and fragments syntheses of natural products always remained one of the top priorities among the synthetic chemists worldwide. Due their curiosity toward the complexity of molecules of living nature and their endeavour to imitate them in laboratory; limitless arrays of natural products have been extracted, architecturally‐elucidated, synthesized, and chronicled by utilizing various synthetic methodologies in different fashions. Frequently, the synthesis of complex natural products proceed with inscrutable synthetic challenges, which can be circumvented either by modification of previously developed synthetic methods or by formulating a new one. In this way, a myriad of powerful synthetic reactions have been developed since the genesis of the logic of chemical synthesis. Amongst them, metathesis tactics discovered unexpectedly in the 1950s (Nobel Prize in 2005), have incredibly influenced and changed the landscape of the art of the total and formal synthesis in the last three A. H. Hoveyda, A. R. Zhugralin, me abruptly as compared to other developed transformations or their modified forms. In this particular review article, we envisioned to report a comprehensive detail of the metathetic tools involved in both total and fragments synthesis of natural products in the years 2018 and 2019 along with an overview of 2017.

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“…8,9 To date, over ten synthetic studies of natural products and medicinal agents have been reported using the original Co(modp) 2 catalyst, improved catalyst systems [e.g., Co(nmp) 2 ], or reductive trapping pathways. Examples include syntheses of gigantetrocin A, 10 asimilobin, 11 mucocin, 12 bullatacin, 13 aplysiallene, 14 asimicin, 15 amphidinolides C and F, 9,16,17 goniotrionin, 18 compound CMI-977 (LDP-977), 19 bovidic acid, 20 cyclocapitelline, 21 and squamotacin C 22 (Figure 1). These impressive accomplishments illustrate the importance and versatility of this highly stereoselective oxidative cyclization.…”

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confidence: 99%

Gram-Scale Synthesis of the Co(nmp)2 Catalyst to Prepare trans-2,5-Disubstituted Tetrahydrofurans by the Aerobic Oxidative Cyclization of Pent-4-en-1-ols

Morra¹,

Morra²,

MacDonald³

et al. 2020

Synthesis

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Co(nmp)2 is an efficient catalyst for the aerobic oxidative cyclization of pent-4-en-1-ols to give 5-hydroxymethyl trans-tetrahydrofurans (THFs) as single diastereomers in high yield. The trans-THF pharmacophore is of interest because it is found in many biologically active natural products. The three-step synthesis of Co(nmp)2 described here gives the catalyst as a fine powder in 80–85% overall yield on 10-gram scale. The use of the catalyst in a representative oxidative cyclization is also described.

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Synthesis of the non-adjacent bis(tetrahydrofuran) core of squamostanin C by silicon-tethered, size-selective triple ring-closing metathesis

Cited by 3 publications

References 39 publications

Stereoselective Synthesis of Conjugated Polyenes Based on Tethered Olefin Metathesis and Carbonyl Olefination: Application to the Total Synthesis of (+)-Bretonin B

Stereoselective Synthesis of Conjugated Polyenes Based on Tethered Olefin Metathesis and Carbonyl Olefination: Application to the Total Synthesis of (+)-Bretonin B

Metathesis Reactions in Natural Product Fragments and Total Syntheses

Gram-Scale Synthesis of the Co(nmp)2 Catalyst to Prepare trans-2,5-Disubstituted Tetrahydrofurans by the Aerobic Oxidative Cyclization of Pent-4-en-1-ols

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