Toward the Creation of Induced Pluripotent Small (iPS) Molecules: Establishment of a Modular Synthetic Strategy for the Heronamide C‑type Polyene Macrolactams and Their Conformational and Reactivity Analysis
A highly modular synthetic strategy for the heronamide C-type polyene macrolactams was established by synthesizing 8-deoxyheronamide C (2). The developed strategy enabled not only the total synthesis of 8-deoxyheronamide C (2) but also the unified synthesis of four heronamide-like molecules named “h...
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| Veröffentlicht in: | Journal of organic chemistry 2021-12, Vol.86 (23), p.16231-16248 |
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| container_title | Journal of organic chemistry |
| container_volume | 86 |
| creator | Kanoh, Naoki Terajima, Yuta Tanaka, Suguru Terashima, Ryusei Nishiyama, Hiromichi Nagasawa, Shota Sasano, Yusuke Iwabuchi, Yoshiharu Nishimura, Shinichi Kakeya, Hideaki |
| description | A highly modular synthetic strategy for the heronamide C-type polyene macrolactams was established by synthesizing 8-deoxyheronamide C (2). The developed strategy enabled not only the total synthesis of 8-deoxyheronamide C (2) but also the unified synthesis of four heronamide-like molecules named “heronamidoids” (5–8). Conformational and reactivity analysis of the heronamidoids clarified that (1) the C19 stereochemistry mainly affected the conformation of the amide linkage, resulting in the change of alignment of two polyene units and reactivity toward photochemical [6π + 6π] cycloaddition, and (2) the C8,C9-diol moiety is important for the conversion to the heronamide A-type skeleton from the heronamide C skeleton. |
| doi_str_mv | 10.1021/acs.joc.1c01760 |
| format | Article |
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The developed strategy enabled not only the total synthesis of 8-deoxyheronamide C (2) but also the unified synthesis of four heronamide-like molecules named “heronamidoids” (5–8). Conformational and reactivity analysis of the heronamidoids clarified that (1) the C19 stereochemistry mainly affected the conformation of the amide linkage, resulting in the change of alignment of two polyene units and reactivity toward photochemical [6π + 6π] cycloaddition, and (2) the C8,C9-diol moiety is important for the conversion to the heronamide A-type skeleton from the heronamide C skeleton.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.1c01760</identifier><identifier>PMID: 34797655</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Cycloaddition Reaction ; Lactams, Macrocyclic ; Molecular Conformation ; Polyenes</subject><ispartof>Journal of organic chemistry, 2021-12, Vol.86 (23), p.16231-16248</ispartof><rights>2021 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a374t-a56037f909fbd3f50c57c04bab3b56511c7abaa39ee88cd2043705ec5728bbe83</citedby><cites>FETCH-LOGICAL-a374t-a56037f909fbd3f50c57c04bab3b56511c7abaa39ee88cd2043705ec5728bbe83</cites><orcidid>0000-0002-4293-7331 ; 0000-0002-4382-3715 ; 0000-0002-3852-8607 ; 0000-0002-5998-3780 ; 0000-0002-9207-4423</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.1c01760$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.1c01760$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34797655$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kanoh, Naoki</creatorcontrib><creatorcontrib>Terajima, Yuta</creatorcontrib><creatorcontrib>Tanaka, Suguru</creatorcontrib><creatorcontrib>Terashima, Ryusei</creatorcontrib><creatorcontrib>Nishiyama, Hiromichi</creatorcontrib><creatorcontrib>Nagasawa, Shota</creatorcontrib><creatorcontrib>Sasano, Yusuke</creatorcontrib><creatorcontrib>Iwabuchi, Yoshiharu</creatorcontrib><creatorcontrib>Nishimura, Shinichi</creatorcontrib><creatorcontrib>Kakeya, Hideaki</creatorcontrib><title>Toward the Creation of Induced Pluripotent Small (iPS) Molecules: Establishment of a Modular Synthetic Strategy for the Heronamide C‑type Polyene Macrolactams and Their Conformational and Reactivity Analysis</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A highly modular synthetic strategy for the heronamide C-type polyene macrolactams was established by synthesizing 8-deoxyheronamide C (2). The developed strategy enabled not only the total synthesis of 8-deoxyheronamide C (2) but also the unified synthesis of four heronamide-like molecules named “heronamidoids” (5–8). 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Conformational and reactivity analysis of the heronamidoids clarified that (1) the C19 stereochemistry mainly affected the conformation of the amide linkage, resulting in the change of alignment of two polyene units and reactivity toward photochemical [6π + 6π] cycloaddition, and (2) the C8,C9-diol moiety is important for the conversion to the heronamide A-type skeleton from the heronamide C skeleton.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>34797655</pmid><doi>10.1021/acs.joc.1c01760</doi><tpages>18</tpages><orcidid>https://orcid.org/0000-0002-4293-7331</orcidid><orcidid>https://orcid.org/0000-0002-4382-3715</orcidid><orcidid>https://orcid.org/0000-0002-3852-8607</orcidid><orcidid>https://orcid.org/0000-0002-5998-3780</orcidid><orcidid>https://orcid.org/0000-0002-9207-4423</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Cycloaddition Reaction Lactams, Macrocyclic Molecular Conformation Polyenes |
| title | Toward the Creation of Induced Pluripotent Small (iPS) Molecules: Establishment of a Modular Synthetic Strategy for the Heronamide C‑type Polyene Macrolactams and Their Conformational and Reactivity Analysis |
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