Methyl ceriferate

Reactions between a-thioallyllithiums and allyl halides, which usually proceed predominantly via OL-CL (head-to-head) coupling, have proved to be valuable in synthesis.They have been used successfully for example in the synthesis of 1,5-dienes such as squalene, (/ )-(-(-)-10,11-epoxyfamesol, (/ )-(+)- and (S)-(-)-2,3-oxidosqualene and mokupalide, dendrolasin, cembra-nolides, methyl ceriferate and Cecropia juvenile hormone (Scheme 25 and Scheme 26). ... 

Marshall, J.A., and DuBay. W.J.. Synthesis of the pseudopterane and furanocembrane ring systems by intraannular cyclization of P and y-alkynyl allylic alcohols, J. Org. Chem., 59, 1703, 1994. Kodama, M., Shiobara, Y., Sumitomo. H.. Fukuzumi, K., Minami, H., and Miyamoto, Y, Synthesis of macrocyclic terpenoids by intramolecular cyclization. Part 10. Total synthesis of methyl ceriferate-1, Tetrahedron Lett., 27, 2157. 1986. 

Kodama, M., Shiobara, Y.. Sumitomo. H.. Fukuzumi, K., Minami, H., and Miyamoto, Y, Synthesis of macrocyclic terpenoids by intramolecular cyclization. Part 12. Total synthesis of methyl ceriferate... 

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