Asymmetric Synthesis of (+)-Geranyllinaloisocyanide: Assignment of Absolute Stereochemistry

Asymmetric Synthesis of (+)-Geranyllinaloisocyanide: Assignment of Absolute Stereochemistry

The first nonracemic synthesis of (+)-geranyllinaloisocyanide, starting with (–)-lactic acid methyl ester, has been accomplished by exploiting a [3.3] sigmatropic rearrangement of allyl cyanate. The synthesis enables assignment of the S configuration of the C(3) isocyano substituted, quaternary ster...

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Veröffentlicht in:Organic letters 2011-05, Vol.13 (10), p.2520-2523
Hauptverfasser: Ichikawa, Yoshiyasu, Matsuda, Yasunori, Okumura, Ken, Nakamura, Mitsuhiro, Masuda, Toshiya, Kotsuki, Hiyoshizo, Nakano, Keiji
Format: Artikel
Sprache:eng
Schlagworte:
Animals
Diterpenes - chemical synthesis
Diterpenes - chemistry
Diterpenes - isolation & purification
Esters
Hawaii
Lactic Acid - analogs & derivatives
Lactic Acid - chemistry
Marine Biology
Molecular Structure
Nitriles - chemical synthesis
Nitriles - chemistry
Nitriles - isolation & purification
Porifera - chemistry
Stereoisomerism
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Zusammenfassung:The first nonracemic synthesis of (+)-geranyllinaloisocyanide, starting with (–)-lactic acid methyl ester, has been accomplished by exploiting a [3.3] sigmatropic rearrangement of allyl cyanate. The synthesis enables assignment of the S configuration of the C(3) isocyano substituted, quaternary stereogenic center in natural geranyllinaloisocyanide.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol200308m