Enantioselective synthesis of (-)-exiguolide by iterative stereoselective dioxinone-directed prins cyclizations

Erika A. Crane; Thomas P. Zabawa; Rebecca L. Farmer; Karl A. Scheidt

doi:10.1002/anie.201102790

Enantioselective synthesis of (-)-exiguolide by iterative stereoselective dioxinone-directed prins cyclizations

Erika A. Crane, Thomas P. Zabawa, Rebecca L. Farmer, Karl A. Scheidt^*

^*Corresponding author for this work

Chemistry

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

57 Scopus citations

Abstract

Three become one: The title compound can be prepared in 26 steps by employing a unified Prins cyclization strategy to construct both tetrahydropyran rings (see scheme). The route combines two similar dioxinone fragments and one aldehyde component to generate the core structure. (-)-Exiguolide selectively inhibits the growth of A549 cancer cells at low concentrations; the triene side chain and the Z-enoate geometry are both necessary for this cytotoxicity.

Original language	English (US)
Pages (from-to)	9112-9115
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	39
DOIs	https://doi.org/10.1002/anie.201102790
State	Published - Sep 19 2011

Keywords

Prins cyclization
antitumor agents
biological activity
dioxinones
total synthesis

ASJC Scopus subject areas

General Chemistry
Catalysis

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/anie.201102790

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abstract = "Three become one: The title compound can be prepared in 26 steps by employing a unified Prins cyclization strategy to construct both tetrahydropyran rings (see scheme). The route combines two similar dioxinone fragments and one aldehyde component to generate the core structure. (-)-Exiguolide selectively inhibits the growth of A549 cancer cells at low concentrations; the triene side chain and the Z-enoate geometry are both necessary for this cytotoxicity.",

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AU - Crane, Erika A.

AU - Zabawa, Thomas P.

AU - Farmer, Rebecca L.

AU - Scheidt, Karl A.

PY - 2011/9/19

Y1 - 2011/9/19

N2 - Three become one: The title compound can be prepared in 26 steps by employing a unified Prins cyclization strategy to construct both tetrahydropyran rings (see scheme). The route combines two similar dioxinone fragments and one aldehyde component to generate the core structure. (-)-Exiguolide selectively inhibits the growth of A549 cancer cells at low concentrations; the triene side chain and the Z-enoate geometry are both necessary for this cytotoxicity.

AB - Three become one: The title compound can be prepared in 26 steps by employing a unified Prins cyclization strategy to construct both tetrahydropyran rings (see scheme). The route combines two similar dioxinone fragments and one aldehyde component to generate the core structure. (-)-Exiguolide selectively inhibits the growth of A549 cancer cells at low concentrations; the triene side chain and the Z-enoate geometry are both necessary for this cytotoxicity.

KW - Prins cyclization

KW - antitumor agents

KW - biological activity

KW - dioxinones

KW - total synthesis

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JO - Angewandte Chemie - International Edition

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ER -

Enantioselective synthesis of (-)-exiguolide by iterative stereoselective dioxinone-directed prins cyclizations

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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