Perillene synthesis

Perilla ketone — see Ketone, 3-furyl isopentyl Perillene synthesis, 4, 668 Perinones, 1, 327, 337 Periodinane, bromo-synthesis, 1, 571 Periodinane, difluoro-reactions, 1, 571 Periodinanes cyclic... 

Such routes have been used for the synthesis of natural products terpenes such as egomaketone (3-(4-methyl-3-pentenoyl)furan, perillene, ar-turmerone and iso-ar-turmerone [341], ar-curcumene [152], artemisia and isoartemisia ketones [342, 343], damascone [344], macrolides such as maysine [345], and pheromones with the sex attractant of the pine saw-fly [346],... 

Reductive cyclization of trichloroethyl propargyl ethers using manganese and catalytic amounts of CrCl2 in the presence of TMSCl provided 3-substituted furans in high yields (Equation 27). The feasibility of this reaction has been demonstrated in the synthesis of the natural products perillene and dendrolasine <20020L1387>. 

Further details of Kondo s perillene (236) synthesis (Vol. 5, p. 43 Vol. 6, p. 16) have been publishedanother synthesis was based (Scheme 4) upon photochemical isomerization-lactonization of (237)/ Reduction and alkylation of 3-methyl-2-furoic acid with l-bromo-3-methylbut-2-ene gave (238) which was oxidatively decarboxylated with lead tetra-acetate-cupric acetate to rosefuran (239). ... 

A synthesis of perillene (295) has been described, following the route from 3-furylmethanol (249) shown in Scheme 9 ... 

The full paper (Vol. 8, p. 58) on the biogenetic-type synthesis of the linalyl oxides has been published and dihydro-ocimenoyl oxide (230) has been synthesized by the regiospecific reaction of 2-methylbutanal with the y-carbon atom of a,a-dimethylallyltrimethylsilane catalysed by TiCU, presumably via cyclization of the corresponding y-chloro-alcohol. ° Straightforward syntheses of perillene (231 X = H,H) and egomaketone (231 X = O) involve prenylation... 

A synthesis of furans from 1,3-dicarbonyl derivatives is shown below. Provide the structure of possible intermediates and discuss in terms of difimctional relationship transformations. [Garst, M. E. Spencer, T. A. General Method for the Synthesis of 3- and 3,4-substituted Furans. Simple Syntheses of perillene and Dendrolasin /. Am. Chem. Soc. 1973, 95, 250-252.] (Difunctional Relationships-13)... 

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