7,7,10-~rimeth~l-~~(~)-octal-2-one (VII) was converted to the cycloethylenedithiolcetal (VIII), which on Raney nickel reduction yielded 7,7,10-trimethyl-~1(g)-octalin (IX). Oxidation with perbenzoic acid led to the corresponding oxide (X), which could be rearranged in low yield to an equilibrium mixture of 7,7,10-trimethyldecal-1-one consisting essentially of the trans-isomer (XI).A convenient modification of the Brown hydration reaction is described, whereby the necessity of generating diborane or of using diglyme is avoided. 7,7,10-~rimetl~~l-~~(~)-octalin (IX) on Brown hydration using this modification stereospecifically furnished 7,7,10/3-trimethyl-cis-decal-1/3-01 (XII), which was oxidized to 7,7,10-trimethyl-cis-decal-1-one (XIII). Isomerization resulted in the above-described equilibrium mixture containing a t least 90% of the trans-isomer (XI). Similarly, the previously described 10-methyl-~l(g)-octalin (XVI) yielded a mixture of the cis-and trans-isomers of 10-methyldecal-1-one (XIX). Syntheses of 2-rnethylene-7,7,10-trimethyl-~1(g)-octalin (XIV) and of 7,7,10-trimethyl-cis-decal-2,3-dione 3-dithiotrimethylene ketal (XXII) are also described.In Part V of this series (1) stereospecific syntheses of the bicyclic ketones (Ia) and (Ib) were described, compounds which could become rings A and B of triterpenes of the P-amyrin (111) type. For the construction of rings D and E, ketones of type (11) are required which are to be joined to the ketones (I) by a two-carbon unit, probably best introduced as acetylene. In this connection a study of the synthesis and stability of 10-methyldecal-1-one has already been carried out (2).The substances of particular interest are the ketones (IIa) and (IIb) of the cis-configuration. Conformational considerations show that the derived acetylenic carbinols on dehydration should give vinyl-acetylenes with the double bond a t the required A1(2)-position, whereas the corresponding trans-ketones would be expected to give vinylacetylenes with the double bond a t the less desirable