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

AGR - Bioscience and Biotechnology for Future Bioindustries

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

2 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

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.9b04074

Fingerprint Dive into the research topics of 'Total Synthesis of Diocollettines A via an Acid-Promoted Oxa-Michael-Aldol-Acetalization Cascade'. Together they form a unique fingerprint.

Cite this

@article{9b99a82bed694811a05f59722f081c6c,

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.",

year = "2019",

month = dec,

day = "20",

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

language = "English",

volume = "21",

pages = "10099--10101",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "24",

}

TY - JOUR

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.

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.

UR - http://www.scopus.com/inward/record.url?scp=85076253122&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85076253122&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.9b04074

DO - 10.1021/acs.orglett.9b04074

M3 - Article

C2 - 31794233

AN - SCOPUS:85076253122

VL - 21

SP - 10099

EP - 10101

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 24

ER -