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A new access to cyclopenta[c]pyridine ring system: syntheses of (−)-plectrodorine and (+)-oxerine

✍ Scribed by Masashi Ohba; Rie Izuta; Emi Shimizu

Book ID
104211369
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
70 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

Total syntheses of (-)-plectrodorine [(-)-1] and (+)-oxerine [(+)-3] possessing the cyclopenta[c]pyridine ring system have been accomplished through a route starting from the chiral g-butyrolactone 7 and exploiting the intramolecular oxazole-olefin Diels-Alder reaction. The sign of specific rotation for the synthetic (+)-3 was in disagreement with that reported for natural oxerine, leaving the absolute configuration of this monoterpene alkaloid incomplete.

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