CYCLIZATION AND REARRANGEMENT OF DITERPENOIDS. II. CYCLIZATION OF cis-LABDA-8,13-DIEN-15-OL BY THE COMPLEX OF TITANIUM TETRACHLORIDE WITH N-METHYLANILINE

Article abstract of DOI:10.1007/BF00575750

It has been shown that the product of the reaction of cis-labda-8,13-dien-15-ol (I) with the complex of TiCl4 (II) and PhNHCH3 (III) is (1R,2R,7S,10S,12S,13S)-13-chloro-2,6,6,10,12-pentamethyltetracyclo<10.2.1.0^1,10.O^2,7>eicosane (IV), the formation on which gives information on the transformation of labdane diterpenoids into tetracycloeicosane derivatives.The reduction of (IV) with LiAlH4.CoCl2 gave the corresponding hydrocarbon.It has been shown that (IV) is formed by the reaction of 13-hydroxy-2,6,6,10,12-pentamethyltetracyclo<10.2.1.0^1,10.O^2,7>eicosane with SOCl2 and ZnCl2.The characteristic of its IR, mass and NMR spectra are given.