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Synthesis of macrocyclic terpenoids by intramolecular cyclization X. Total synthesis of methyl ceriferate-I

✍ Scribed by Mitsuaki Kodama; Yoshinori Shiobara; Hisako Sumitomo; Kazuyoshi Fukuzumi; Hiroyuki Minami; Yasuko Miyamoto


Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
279 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis


The methyl ester of f+)-ceriferic acid-I, a 14-membered ring sesterterpene isolated from the wax of the scale insect Ceroplastes ceriferus, was synthesized by means of an intramolecular Ylttig-type reaction.


πŸ“œ SIMILAR VOLUMES


Synthesis of macrocyclic terpenoids by i
✍ Mitsuaki Kodama; Shunichi Yokoo; Yasuo Matsuki; ShΓ΄ ItΓ΄ πŸ“‚ Article πŸ“… 1979 πŸ› Elsevier Science 🌐 French βš– 256 KB

Thermal rearrangement and acid-catalyzed cyclization of all possible geometrical isomers of hedycaryol were investigated. From the stereochemistry of the products, the reacting conformations were deduced. While three (E,E-, E,Z- AND Z,E-) isomers reacted through the crossed conformations, Z,Z-isomer

Synthesis of macrocyclic terpenoids by i
✍ Mitsuaki Kodama; Toshiya Takahashi; Tsutomu Kojima; Sho Ito πŸ“‚ Article πŸ“… 1988 πŸ› Elsevier Science 🌐 French βš– 722 KB

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