Enantioselective total synthesis of the osteoclastogenesis inhibitor (+)-symbioimine

Justin Kim; Regan James Thomson

doi:10.1002/anie.200605160

Enantioselective total synthesis of the osteoclastogenesis inhibitor (+)-symbioimine

Justin Kim^*, Regan James Thomson

^*Corresponding author for this work

Chemistry

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

26 Scopus citations

Abstract

(Chemical Equation Presented) No bones about it: The first enantioselective total synthesis of the osteoclastogenesis inhibitor (+)-symbioimine (1) has been achieved. The synthesis features a convergent enol silane addition to a dimethyl acetal and a key, possibly biomimetic, intramolecular Diels-Alder reaction promoted by a dihydropyridinium ion to build four of the five requisite stereocenters in one step.

Original language	English (US)
Pages (from-to)	3104-3106
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	46
Issue number	17
DOIs	https://doi.org/10.1002/anie.200605160
State	Published - Jun 29 2007

Keywords

Biomimetic synthesis
Cycloaddition
Diels-Alder reaction
Natural products
Total synthesis

ASJC Scopus subject areas

Chemistry(all)

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10.1002/anie.200605160

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abstract = "(Chemical Equation Presented) No bones about it: The first enantioselective total synthesis of the osteoclastogenesis inhibitor (+)-symbioimine (1) has been achieved. The synthesis features a convergent enol silane addition to a dimethyl acetal and a key, possibly biomimetic, intramolecular Diels-Alder reaction promoted by a dihydropyridinium ion to build four of the five requisite stereocenters in one step.",

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AU - Thomson, Regan James

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AB - (Chemical Equation Presented) No bones about it: The first enantioselective total synthesis of the osteoclastogenesis inhibitor (+)-symbioimine (1) has been achieved. The synthesis features a convergent enol silane addition to a dimethyl acetal and a key, possibly biomimetic, intramolecular Diels-Alder reaction promoted by a dihydropyridinium ion to build four of the five requisite stereocenters in one step.

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KW - Diels-Alder reaction

KW - Natural products

KW - Total synthesis

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Enantioselective total synthesis of the osteoclastogenesis inhibitor (+)-symbioimine

Abstract

Keywords

ASJC Scopus subject areas

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