Enantiocontrolled Synthesis of Jasmonates via Tandem Retro-Diels−Alder−Ene Reaction Activated by a Silyl Substituent

Enantiocontrolled Synthesis of Jasmonates via Tandem Retro-Diels−Alder−Ene Reaction Activated by a Silyl Substituent

An enantiocontrolled synthesis of (−)-methyl 6-epi-cucurbate and (+)-methyl jasmonate was established from a chiral tricyclic lactone via a new type of tandem retro-Diels−Alder−ene reaction activated by a trimethysilyl substituent as the key step.

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Veröffentlicht in:Organic letters 2004-02, Vol.6 (3), p.409-411
Hauptverfasser: Suzuki, Katsufumi, Inomata, Kohei, Endo, Yasuyuki
Format: Artikel
Sprache:eng
Schlagworte:
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Lactams - chemical synthesis
Lactams - chemistry
Molecular Structure
Oxylipins
Plant Growth Regulators - chemical synthesis
Plant Growth Regulators - chemistry
Stereoisomerism
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Zusammenfassung:An enantiocontrolled synthesis of (−)-methyl 6-epi-cucurbate and (+)-methyl jasmonate was established from a chiral tricyclic lactone via a new type of tandem retro-Diels−Alder−ene reaction activated by a trimethysilyl substituent as the key step.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol036253p