A Reductive-Heck Approach to the Hydroazulene Ring System: A Formal Synthesis of the Englerins

Gao, Peng; Cook, Silas P.

doi:10.1021/ol3013167

Cited by 90 publications

(32 citation statements)

References 56 publications

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“…Gao et al. described synthetic access to the hydroazulene ring system . Reductive‐Heck reaction, in combination with transannular epoxide rearrangement cascade, opened up a new synthetic route to the guaiane core of the englerins.…”

Section: Intramolecular Approachmentioning

confidence: 99%

Reductive Heck Reaction: An Emerging Alternative in Natural Product Synthesis

Ghosh

2019

ChemistrySelect

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Metal‐catalyzed cross coupling reactions are efficient synthetic methods and developing continuously for the synthesis of diverse range of heterocycles, found in wide range of natural products. Among others, reductive Heck reaction has elegantly been employed to access various natural products. This review article covers the updated summary of relevant literature on the application of reductive Heck reaction for the synthesis of natural products. Discussion on the underlying mechanistic rationale has also been included wherever felt necessary.

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Section: Intramolecular Approachmentioning

confidence: 99%

Reductive Heck Reaction: An Emerging Alternative in Natural Product Synthesis

Ghosh

2019

ChemistrySelect

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“…The formation of 3 is probably due to the sluggishness of the NiH elimination, which allows for the competitive protonation of the fragile intermediate alkylnickel 2 -Ni. While the Pd-catalyzed reductive Heck reaction promoted by a hydride generated in situ is well known [23–24], the nickel-catalyzed process is likely to occur through a radical hydrogen transfer from the DMF [20,25]. The N -allylaniline 1c gives the same good yield added to an attractive ( 2c + 2c’ )/ 3c ratio of 87/13 (Table 1, entry 3).…”

Section: Resultsmentioning

confidence: 99%

Intramolecular carbonickelation of alkenes

Lhermet¹,

Durandetti²,

Maddaluno³

2013

Beilstein J. Org. Chem.

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SummaryThe efficiency of the intramolecular carbonickelation of substituted allylic ethers and amines has been studied to evaluate the influence of the groups borne by the double bond on this cyclization. The results show that when this reaction takes place, it affords only the 5-exo-trig cyclization products, viz. dihydrobenzofurans or indoles. Depending on the tethered heteroatom (O or N), the outcome of the cyclization differs. While allylic ethers are relatively poor substrates that undergo a side elimination and need an intracyclic double bond to proceed, allylic amines react well and afford indoline and indole derivatives. Finally, the synthesis of the trinuclear ACE core of a morphine-like skeleton was achieved by using NiBr2bipy catalysis.

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“…Exploration of conditions for the reductive Heck cyclization were met with limited success (Table 1, entry 2). [24] Although synthetically useful ratios of 22/23 could be obtained, we noted a significant amount of alkyne 24 in the reaction mixture. The formation of 24, however, opened the possibility of conducting a radical-based reductive cyclization to 22.…”

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confidence: 77%