ent-Kaurane Diterpenoids from Chinese Liverworts and Their Antitumor Activities through Michael Addition As Detected in Situ by a Fluorescence Probe

We have developed a dearomatization-rearomatization strategy for modification of peptides/protein through thiol-Michael addition to the electrophilic cyclohexadienone intermediate in situ generated by oxidation of tyrosine. This strategy enriches the conjugation...

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Cu-Catalyzed one-pot synthesis of thiochromeno-quinolinone and thiochromeno-thioflavone via oxidative double hetero Michael addition using in situ generated nucleophiles

Chemical Communications ◽

10.1039/d0cc03210g ◽

2020 ◽

Vol 56 (62) ◽

pp. 8826-8829

Author(s):

Nallappan Sundaravelu ◽

Govindasamy Sekar

Keyword(s):

Michael Addition ◽

One Pot ◽

One Pot Synthesis

A copper catalyzed three-component synthesis of π-conjugated tetracyclic thiochromeno-quinolinone and thiochromeno-thioflavone was established via oxidative double hetero Michael addition using in situ generated nucleophiles.

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Intramolecular Michael Addition of N- and O-Centred Nucleophiles to Tethered Acrylates. The Role of Double-Bond Geometry in Controlling the Diastereo- selectivity of Cyclizations Leading to 2,6-Disubstituted Tetrahydropyrans and Piperidines.

Australian Journal of Chemistry ◽

10.1071/c97173 ◽

1998 ◽

Vol 51 (1) ◽

pp. 9 ◽

Cited By ~ 28

Author(s):

Martin G. Banwell ◽

Brett D. Bissett ◽

Chinh T. Bui ◽

Ha T. T. Pham ◽

Gregory W. Simpson

Keyword(s):

Double Bond ◽

Total Synthesis ◽

Michael Addition ◽

Reductive Amination ◽

Major Product ◽

Enantioselective Synthesis ◽

Cyclization Reactions ◽

Glandular Secretion

The oxyanion derived from hydroxyacrylate E-(5) undergoes smooth intramolecular Michael addition to give the trans-2,6-disubstituted tetrahydropyran (7) as the major product of reaction. In contrast, the oxyanion obtained from isomer Z-(5) cyclizes to give the cis-2,6-disubstituted tetrahydropyran (6) as the major product. Such chemistry has been extended to the enantioselective synthesis of (+)-(6) the acquisition of which constitutes a formal total synthesis of acid (+)-(2), a constituent of the glandular secretion from the civet cat (Viverra civetta). Reductive amination of keto acrylate (12) affords an intermediate amine which cyclizes, in situ, to give the cis-2,6-disubstituted piperidine (26). Analogous treatment of compound (13) delivers the isomeric trans-2,6-disubstituted piperidine (27) as the exclusive product of reaction. Transition state structures have been proposed to account for the diastereoselectivities observed in all of the cyclization reactions.

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Stereocontrolled construction of six vicinal stereogenic centers on a hexahydroxanthone framework through a formal [2+1+3] annulation

Chemical Communications ◽

10.1039/c9cc08101a ◽

2019 ◽

Vol 55 (93) ◽

pp. 14003-14006 ◽

Cited By ~ 11

Author(s):

Shun-Qin Chang ◽

Xiong Zou ◽

Yi Gong ◽

Xue-Wen He ◽

Xiong-Li Liu ◽

...

Keyword(s):

Michael Addition ◽

One Pot ◽

Stereogenic Centers

The first example of a bifunctional donor–donor 3C synthon formed in situ from an activated methine with nitromethane through a [2+1] Michael addition, further directing a one-pot organocascade Michael/Henry cycloaddition was developed.

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