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 intramolecular cyclization IV. Synthesis of 6z-hedycaryols
✍ Scribed by Mitsuaki Kodama; Shun-ichi Yokoo; Harutami Yamada; Shô Itô
- Publisher
- Elsevier Science
- Year
- 1978
- Tongue
- French
- Weight
- 232 KB
- Volume
- 19
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
Recently,
we have reported the successful synthesis of natural hedycaryal l_ (PE,6E-isomer) and 2Z,6E-'0)
1')
'2)
📜 SIMILAR VOLUMES
Two 14-membered diterpenes, 3Z-cembrene A and cembrenene, isolated from a 1) 2) 3) 4) References and Notes M. Kodama, Y. Matsuki and S. lt8, Tetrahedron Letters 3065 (1975). -I
Stereoselectrve totol synthesis of (f)-cubitene, o diterpane isolated from termite soldiers, and its stereoisomer has been achieved util rzing the anion-induced intramolecular cyclization.
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.
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