Total Synthesis of Boletopsin 11 Enabled by Directed ortho-C(sp2)-H Arylation

Meng Yao Zhang; Russell A. Barrow

doi:10.1021/acs.joc.8b00792

Total Synthesis of Boletopsin 11 Enabled by Directed ortho-C(sp²)-H Arylation

Meng Yao Zhang, Russell A. Barrow^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

A nine-step synthesis of boletopsin 11 (1), a bioactive fungal natural product, is disclosed. Key features include a one-pot [O]-oxa-Michael cascade to establish the polyoxygenated dibenzofuran core followed by a Pd-catalyzed directed ortho-C(sp²)-H arylation to complete the fully functionalized carbon skeleton. Exploration of the latter transformation led to the discovery of an unexpected tandem ortho-C(sp²)-H arylation event, and the scope of the directed ortho-C(sp²)-H reaction was further investigated with coupling partners varying in stereoelectronic properties.

Original language	English
Pages (from-to)	6776-6782
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	83
Issue number	12
DOIs	https://doi.org/10.1021/acs.joc.8b00792
Publication status	Published - 15 Jun 2018

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title = "Total Synthesis of Boletopsin 11 Enabled by Directed ortho-C(sp2)-H Arylation",

abstract = "A nine-step synthesis of boletopsin 11 (1), a bioactive fungal natural product, is disclosed. Key features include a one-pot [O]-oxa-Michael cascade to establish the polyoxygenated dibenzofuran core followed by a Pd-catalyzed directed ortho-C(sp2)-H arylation to complete the fully functionalized carbon skeleton. Exploration of the latter transformation led to the discovery of an unexpected tandem ortho-C(sp2)-H arylation event, and the scope of the directed ortho-C(sp2)-H reaction was further investigated with coupling partners varying in stereoelectronic properties.",

author = "Zhang, {Meng Yao} and Barrow, {Russell A.}",

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AU - Barrow, Russell A.

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N2 - A nine-step synthesis of boletopsin 11 (1), a bioactive fungal natural product, is disclosed. Key features include a one-pot [O]-oxa-Michael cascade to establish the polyoxygenated dibenzofuran core followed by a Pd-catalyzed directed ortho-C(sp2)-H arylation to complete the fully functionalized carbon skeleton. Exploration of the latter transformation led to the discovery of an unexpected tandem ortho-C(sp2)-H arylation event, and the scope of the directed ortho-C(sp2)-H reaction was further investigated with coupling partners varying in stereoelectronic properties.

AB - A nine-step synthesis of boletopsin 11 (1), a bioactive fungal natural product, is disclosed. Key features include a one-pot [O]-oxa-Michael cascade to establish the polyoxygenated dibenzofuran core followed by a Pd-catalyzed directed ortho-C(sp2)-H arylation to complete the fully functionalized carbon skeleton. Exploration of the latter transformation led to the discovery of an unexpected tandem ortho-C(sp2)-H arylation event, and the scope of the directed ortho-C(sp2)-H reaction was further investigated with coupling partners varying in stereoelectronic properties.

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JF - Journal of Organic Chemistry

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ER -

Total Synthesis of Boletopsin 11 Enabled by Directed ortho-C(sp²)-H Arylation

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