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

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

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

Organic letters, 12/2019, Volume: 21, Issue: 24

Journal Article

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

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