Selective Synthesis of (+)-Dysoline

Aaron Coffin; Joseph M. Ready

doi:10.1021/acs.orglett.8b03777

Selective Synthesis of (+)-Dysoline

Aaron Coffin, Joseph M. Ready

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

7 Scopus citations

Abstract

Dysoline, a novel chromone alkaloid isolated from Dysoxylum binectariferum, was reported to have selective cytotoxicity for HT1080 fibrosarcoma cells (IC ₅₀ of 0.21 μM). Given the scarcity of natural material, a concise synthesis of (+)-dysoline was developed, allowing for further biological evaluation. An enantioselective nucleophile-catalyzed aldol lactonization formed the piperidine ring with control of relative and absolute stereochemistry. Construction of the C6-chromone core with complete regioselectivity was achieved using a Danheiser benzannulation.

Original language	English (US)
Pages (from-to)	648-651
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	3
DOIs	https://doi.org/10.1021/acs.orglett.8b03777
State	Published - Feb 1 2019

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.8b03777

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abstract = " Dysoline, a novel chromone alkaloid isolated from Dysoxylum binectariferum, was reported to have selective cytotoxicity for HT1080 fibrosarcoma cells (IC 50 of 0.21 μM). Given the scarcity of natural material, a concise synthesis of (+)-dysoline was developed, allowing for further biological evaluation. An enantioselective nucleophile-catalyzed aldol lactonization formed the piperidine ring with control of relative and absolute stereochemistry. Construction of the C6-chromone core with complete regioselectivity was achieved using a Danheiser benzannulation.",

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AU - Ready, Joseph M.

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AB - Dysoline, a novel chromone alkaloid isolated from Dysoxylum binectariferum, was reported to have selective cytotoxicity for HT1080 fibrosarcoma cells (IC 50 of 0.21 μM). Given the scarcity of natural material, a concise synthesis of (+)-dysoline was developed, allowing for further biological evaluation. An enantioselective nucleophile-catalyzed aldol lactonization formed the piperidine ring with control of relative and absolute stereochemistry. Construction of the C6-chromone core with complete regioselectivity was achieved using a Danheiser benzannulation.

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JO - Organic Letters

JF - Organic Letters

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Selective Synthesis of (+)-Dysoline

Abstract

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