Toward the Total Synthesis of Amphidinolide N: Synthesis of the C8-C29 Fragment

Yuki Kawashima; Atsushi Toyoshima; Haruhiko Fuwa; Makoto Sasaki

doi:10.1021/acs.orglett.6b00871

Toward the Total Synthesis of Amphidinolide N: Synthesis of the C8-C29 Fragment

Yuki Kawashima, Atsushi Toyoshima, Haruhiko Fuwa, Makoto Sasaki

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

10 Citations (Scopus)

Abstract

A synthesis of the C8-C29 fragment of amphidinolide N, a potent cytotoxic macrolide isolated from the marine dinoflagellate Amphidinium sp., has been achieved. The key features of the synthesis involve a convergent union of the C9-C15 and C16-C29 fragments by Steglich esterification and the construction of a pyran unit through a Tebbe methylenation/ring-closing metathesis sequence.

Original language	English
Pages (from-to)	2232-2235
Number of pages	4
Journal	Organic letters
Volume	18
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.6b00871
Publication status	Published - 2016 May 6

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.6b00871

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title = "Toward the Total Synthesis of Amphidinolide N: Synthesis of the C8-C29 Fragment",

abstract = "A synthesis of the C8-C29 fragment of amphidinolide N, a potent cytotoxic macrolide isolated from the marine dinoflagellate Amphidinium sp., has been achieved. The key features of the synthesis involve a convergent union of the C9-C15 and C16-C29 fragments by Steglich esterification and the construction of a pyran unit through a Tebbe methylenation/ring-closing metathesis sequence.",

author = "Yuki Kawashima and Atsushi Toyoshima and Haruhiko Fuwa and Makoto Sasaki",

note = "Funding Information: We thank Kaneka Corporation for donating (S)-Roche ester. This work was financially supported in part by a Grants-in-Aid for Scientific Research (B) (25282228) and Scientific Research on Innovative Areas {"}Chemical Biology of Natural Products{"} (23102016)37 from the Japan Society for the Promotion of Science (JSPS).",

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T1 - Toward the Total Synthesis of Amphidinolide N

T2 - Synthesis of the C8-C29 Fragment

AU - Kawashima, Yuki

AU - Toyoshima, Atsushi

AU - Fuwa, Haruhiko

AU - Sasaki, Makoto

N1 - Funding Information: We thank Kaneka Corporation for donating (S)-Roche ester. This work was financially supported in part by a Grants-in-Aid for Scientific Research (B) (25282228) and Scientific Research on Innovative Areas "Chemical Biology of Natural Products" (23102016)37 from the Japan Society for the Promotion of Science (JSPS).

PY - 2016/5/6

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N2 - A synthesis of the C8-C29 fragment of amphidinolide N, a potent cytotoxic macrolide isolated from the marine dinoflagellate Amphidinium sp., has been achieved. The key features of the synthesis involve a convergent union of the C9-C15 and C16-C29 fragments by Steglich esterification and the construction of a pyran unit through a Tebbe methylenation/ring-closing metathesis sequence.

AB - A synthesis of the C8-C29 fragment of amphidinolide N, a potent cytotoxic macrolide isolated from the marine dinoflagellate Amphidinium sp., has been achieved. The key features of the synthesis involve a convergent union of the C9-C15 and C16-C29 fragments by Steglich esterification and the construction of a pyran unit through a Tebbe methylenation/ring-closing metathesis sequence.

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Toward the Total Synthesis of Amphidinolide N: Synthesis of the C8-C29 Fragment

Abstract

ASJC Scopus subject areas

UN SDGs

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