Total Synthesis of Diocollettines A via an Acid-Promoted Oxa-Michael-Aldol-Acetalization Cascade

Misaki Kawamoto; Shuntaro Sato; Masaru Enomoto; Yusuke Ogura; Shigefumi Kuwahara

doi:10.1021/acs.orglett.9b04074

Total Synthesis of Diocollettines A via an Acid-Promoted Oxa-Michael-Aldol-Acetalization Cascade

Misaki Kawamoto, Shuntaro Sato, Masaru Enomoto, Yusuke Ogura, Shigefumi Kuwahara

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

4 Citations (Scopus)

Abstract

A diastereo- and enantioselective total synthesis of diocollettines A with an unusual oxygen-containing tricyclic ring system has been achieved in 63% overall yield from commercially available 3-phenylpropanal via four steps. The key feature of the present synthesis is an exclusively diastereoselective cascade sequence composed of a trans-selective oxa-Michael addition of 1,3-dihydroxyacetone to a 2,3-dihydropyrylium ion intermediate, intramolecular aldol-type reaction, and intramolecular acetalization.

Original language	English
Pages (from-to)	10099-10101
Number of pages	3
Journal	Organic letters
Volume	21
Issue number	24
DOIs	https://doi.org/10.1021/acs.orglett.9b04074
Publication status	Published - 2019 Dec 20
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.9b04074

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title = "Total Synthesis of Diocollettines A via an Acid-Promoted Oxa-Michael-Aldol-Acetalization Cascade",

abstract = "A diastereo- and enantioselective total synthesis of diocollettines A with an unusual oxygen-containing tricyclic ring system has been achieved in 63% overall yield from commercially available 3-phenylpropanal via four steps. The key feature of the present synthesis is an exclusively diastereoselective cascade sequence composed of a trans-selective oxa-Michael addition of 1,3-dihydroxyacetone to a 2,3-dihydropyrylium ion intermediate, intramolecular aldol-type reaction, and intramolecular acetalization.",

author = "Misaki Kawamoto and Shuntaro Sato and Masaru Enomoto and Yusuke Ogura and Shigefumi Kuwahara",

note = "Funding Information: This work was financially supported by AMED (Grant No. JP19am0101100). We are grateful to Ms. Yuka Taguchi (Tohoku University) for her help with NMR and MS measurements. Funding Information: This work was financially supported by AMED (Grant No. JP19am0101100). We are grateful to Ms. Yuka Taguchi (Tohoku University) for her help with NMR and MS measurements. Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

year = "2019",

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doi = "10.1021/acs.orglett.9b04074",

language = "English",

volume = "21",

pages = "10099--10101",

journal = "Organic Letters",

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publisher = "American Chemical Society",

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T1 - Total Synthesis of Diocollettines A via an Acid-Promoted Oxa-Michael-Aldol-Acetalization Cascade

AU - Kawamoto, Misaki

AU - Sato, Shuntaro

AU - Enomoto, Masaru

AU - Ogura, Yusuke

AU - Kuwahara, Shigefumi

N1 - Funding Information: This work was financially supported by AMED (Grant No. JP19am0101100). We are grateful to Ms. Yuka Taguchi (Tohoku University) for her help with NMR and MS measurements. Funding Information: This work was financially supported by AMED (Grant No. JP19am0101100). We are grateful to Ms. Yuka Taguchi (Tohoku University) for her help with NMR and MS measurements. Publisher Copyright: Copyright © 2019 American Chemical Society.

PY - 2019/12/20

Y1 - 2019/12/20

N2 - A diastereo- and enantioselective total synthesis of diocollettines A with an unusual oxygen-containing tricyclic ring system has been achieved in 63% overall yield from commercially available 3-phenylpropanal via four steps. The key feature of the present synthesis is an exclusively diastereoselective cascade sequence composed of a trans-selective oxa-Michael addition of 1,3-dihydroxyacetone to a 2,3-dihydropyrylium ion intermediate, intramolecular aldol-type reaction, and intramolecular acetalization.

AB - A diastereo- and enantioselective total synthesis of diocollettines A with an unusual oxygen-containing tricyclic ring system has been achieved in 63% overall yield from commercially available 3-phenylpropanal via four steps. The key feature of the present synthesis is an exclusively diastereoselective cascade sequence composed of a trans-selective oxa-Michael addition of 1,3-dihydroxyacetone to a 2,3-dihydropyrylium ion intermediate, intramolecular aldol-type reaction, and intramolecular acetalization.

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ER -

Total Synthesis of Diocollettines A via an Acid-Promoted Oxa-Michael-Aldol-Acetalization Cascade

Abstract

ASJC Scopus subject areas

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