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Syntheses of macrocyclic terpenoids by intramolecular cyclization I. (±)-cembrene-a, a termite trail pheromone, and (±)-nephthenol

✍ Scribed by Mitsuaki Kodama; Yasuo Matsuki; Shô Itô


Publisher
Elsevier Science
Year
1975
Tongue
French
Weight
199 KB
Volume
16
Category
Article
ISSN
0040-4039

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Syntheses of macrocyclic terpenoids by i
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ln the previous paper (l), we have reported an efficient anion-induced intramolecular cyclizatian of the epoxy sulfide ,l\_ leading to the fourteen-membered ring compound ,2\_. We have extended our study starting from 2 to induce the other functionalities incorporated in the naturally occurring cemb

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Stereoselective synthesis of cubitene (11, a novel diterp-ene isolated from defense secretion of termites, has been accomplished using an intramolecular reaction of a-sulfenyl carbanion vi th epoxide. Hydride reduction of the ketone 11 obtalned by Claisen rearrangement occurred in unexpectedly high