2021
DOI: 10.1002/ajoc.202100691
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Synthetic Approaches to Crinipellin Based Tetraquinanes via Ring‐Rearrangement Metathesis and Ring‐Closing Metathesis

Abstract: Herein, we have studied the synthetic approaches to tetraquinanes that are present in crinipellin type natural products by employing ring-rearrangement metathesis (RRM) and ring-closing metathesis (RCM) as key steps. These studies involve finding the suitable alkylation sequence to prepare desired RRM/RCM precursors. Methyl-tetraquinane has been assembled by employing a regio-, and stereoselective methylation followed by allylation sequence. Whereas, allyltetraquinane was constructed by following the allylatio… Show more

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Cited by 13 publications
(9 citation statements)
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“…Here, the low yield of 66 is due to the fusion between the olefinic moieties E and F is relatively less favored as it leads to a bridged bicyclic system which is known to have a considerable amount of ring strain and therefore formed as a minor product in all the cases. The structure of compound 66 was confirmed by NMR data as it exhibits different δ values as compared with compounds 52 , 67 , and 68 . The remaining double bonds A and F , C and E , and D and E are in the most favorable dispositions and therefore more likely to deliver the corresponding RRM products 18 and 19 as the major compounds.…”
Section: Results and Discussionmentioning
confidence: 99%
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“…Here, the low yield of 66 is due to the fusion between the olefinic moieties E and F is relatively less favored as it leads to a bridged bicyclic system which is known to have a considerable amount of ring strain and therefore formed as a minor product in all the cases. The structure of compound 66 was confirmed by NMR data as it exhibits different δ values as compared with compounds 52 , 67 , and 68 . The remaining double bonds A and F , C and E , and D and E are in the most favorable dispositions and therefore more likely to deliver the corresponding RRM products 18 and 19 as the major compounds.…”
Section: Results and Discussionmentioning
confidence: 99%
“…The structure of compound 66 was confirmed by NMR data as it exhibits different δ values as compared with compounds 52, 67, and 68. 41 The remaining double bonds A and F, C and E, and D and E are in the most favorable dispositions and therefore more likely to deliver the corresponding RRM products 18 and 19 as the major compounds.…”
Section: ■ Results and Discussionmentioning
confidence: 99%
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“…Similarly, the triallyl derivative 83 undergo the RRM sequence in the presence of G‐II catalyst to produce tetraquinane 87 (Scheme 9). [9f] …”
Section: Model Studies and Total Synthesis Of Crinipellinmentioning
confidence: 99%