Total Synthesis of Dalesconol A by Pd(0)/Norbornene-Catalyzed Three-Fold Domino Reaction and Pd(II)-Catalyzed Trihydroxylation

Guo, Yun; Luan, Xinjun

doi:10.1021/jacs.1c12118

Cited by 27 publications

(8 citation statements)

References 62 publications

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“…Luckily, the check with Co(OAc) 2 ·4H 2 O/KBr/O 2 /PPh 3 /NHPI, a protocol from Zeng and co-workers, led to the formation of 4 in 33% yield. However, the desired oxidation cannot be observed under Luan’s condition, NHPI/CuCl/O 2 in PhCN . During our study on the NHPI-mediated benzylic aerobic oxidation of 20 , it was demonstrated that different cobalt salts and bromide salts had evident effects on this process .…”

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confidence: 81%

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Total Synthesis of (−)-Ceforalide B and (−)-Cephanolides B–D

et al. 2022

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Metrics & More Article Recommendations * sı Supporting Information ABSTRACT: (−)-Ceforalide B (1) and (−)-cephanolides B−D (2−4) are benzenoid cephanolide diterpenoids possessing the same pentacyclic skeleton, which contains three C 13 −C 15 substituent patterns and different benzylic oxidation states. An olefination/6π-electrocyclization/oxidative aromatization cascade has been verified as divergent access to three C 13 −C 15 patterns. The benzylic aerobic oxidations enabled by the Co(OAc) 2 •4H 2 O/ bromide salt/O 2 /PPh 3 /N-hydroxyphthalimide system have been developed to deliver expected site-selectivity and different oxidation states. Through the divergent strategy, total synthesis of (−)-ceforalide B and (−)-cephanolides B−D is accomplished.

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confidence: 81%

“…However, the desired oxidation cannot be observed under Luan's condition, NHPI/CuCl/O 2 in PhCN. 18 During our study on the NHPI-mediated benzylic aerobic oxidation of 20, it was demonstrated that different cobalt salts and bromide salts had evident effects on this process. 19 obtained as the minor product.…”

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confidence: 88%

Total Synthesis of (−)-Ceforalide B and (−)-Cephanolides B–D

et al. 2022

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“…Polycyclic aromatic hydrocarbons (PAHs) have attracted much attention due to their novel optoelectronic, self-assembly, and charge-transport properties resulting from their unique π-conjugated scaffold. − Therefore, synthetic strategies to produce PAHs have been extensively explored. In 2015, the Wen group disclosed palladium-catalyzed insertion of internal alkynes into cyclic diaryliodoniums via [4 + 2] benzannulation to generate various phenanthrenes, one of the vital molecular structural features in functional materials .…”

Section: Synthetic Applications Of Cyclic Aryliodoniumsmentioning

confidence: 99%

Recent Progress in Cyclic Aryliodonium Chemistry: Syntheses and Applications

et al. 2023

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Hypervalent aryliodoumiums are intensively investigated as arylating agents. They are excellent surrogates to aryl halides, and moreover they exhibit better reactivity, which allows the corresponding arylation reactions to be performed under mild conditions. In the past decades, acyclic aryliodoniums are widely explored as arylation agents. However, the unmet need for acyclic aryliodoniums is the improvement of their notoriously low reaction economy because the coproduced aryl iodides during the arylation are often wasted. Cyclic aryliodoniums have their intrinsic advantage in terms of reaction economy, and they have started to receive considerable attention due to their valuable synthetic applications to initiate cascade reactions, which can enable the construction of complex structures, including polycycles with potential pharmaceutical and functional properties. Here, we are summarizing the recent advances made in the research field of cyclic aryliodoniums, including the nascent design of aryliodonium species and their synthetic applications. First, the general preparation of typical diphenyl iodoniums is described, followed by the construction of heterocyclic iodoniums and monoaryl iodoniums. Then, the initiated arylations coupled with subsequent domino reactions are summarized to construct polycycles. Meanwhile, the advances in cyclic aryliodoniums for building biaryls including axial atropisomers are discussed in a systematic manner. Finally, a very recent advance of cyclic aryliodoniums employed as halogen-bonding organocatalysts is described.

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“…In the past few decades, domino reactions under the catalysis of palladium complexes have made significant progress. Noteworthy among them is the Catellani reaction based on palladium/norbornene catalysis, serving as an efficient strategy to synthesize polysubstituted aromatics . Meanwhile, palladium-catalyzed domino reactions via a retro-Diels–Alder strategy have received intense attention in recent years.…”

Section: Introductionmentioning

confidence: 99%

Computational Determination of the Mechanism of the Palladium-Catalyzed Domino Reaction of ortho-Iodostyrene, Oxanorbornadiene, and Phenylboronic Acid

Han,

Zhao,

et al. 2023

J. Org. Chem.

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The palladium-catalyzed three-component domino reaction of ortho-iodostyrene, 2,3-dicarbomethoxy-7-oxanorbornadiene (ONBD), and phenylboronic acid discovered by the Lautens group provides a convenient method to synthesize indenes derivatives. Herein, density functional theory (DFT) calculations were employed to explore the detailed mechanism of this domino reaction. The computational results suggest that the alkeneinsertion-first and the transmetalation-first mechanisms are competitive, and the former mechanism is slightly more favorable because of the difficult intramolecular alkene insertion of the alkyl-Pd II -aryl than alkyl-Pd II -I complex. Further analysis on substituents of ONBD unveils the impacts of noncovalent interactions and electronic effect on the rate-determining retro-Diels−Alder process. The understanding of this domino reaction has important implications for developing a novel palladium-catalyzed domino reaction with a retro-Diels−Alder strategy.

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Total Synthesis of Dalesconol A by Pd(0)/Norbornene-Catalyzed Three-Fold Domino Reaction and Pd(II)-Catalyzed Trihydroxylation

Cited by 27 publications

References 62 publications

Total Synthesis of (−)-Ceforalide B and (−)-Cephanolides B–D

Total Synthesis of (−)-Ceforalide B and (−)-Cephanolides B–D

Recent Progress in Cyclic Aryliodonium Chemistry: Syntheses and Applications

Computational Determination of the Mechanism of the Palladium-Catalyzed Domino Reaction of ortho-Iodostyrene, Oxanorbornadiene, and Phenylboronic Acid

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