Reaction SMILES: [CH3:1][O:2][Sn:3]([CH2:12][CH2:13][CH2:14][CH3:15])([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:4][CH2:5][CH2:6][CH3:7].C(OC1[C:29]2[C:24](=[CH:25][C:26]([Cl:30])=[CH:27][CH:28]=2)[CH2:23][CH2:22][CH:21]=1)(=O)C>>[Cl:30][C:26]1[CH:25]=[C:24]2[C:29](=[CH:28][CH:27]=1)[C:1]([O:2][Sn:3]([CH2:8][CH2:9][CH2:10][CH3:11])([CH2:4][CH2:5][CH2:6][CH3:7])[CH2:12][CH2:13][CH2:14][CH3:15])=[CH:21][CH2:22][CH2:23]2
Reactant: CCCC[Sn](CCCC)(CCCC)OC
Reactant: CC(=O)OC1=CCCc2cc(Cl)ccc21
Product: CCCC[Sn](CCCC)(CCCC)OC1=CCCc2cc(Cl)ccc21

Procedure:
In accordance with synthesis scheme 3, 1 mol of known 6-chloro-1-tetralone is refluxed for 5 h together with 2 mol of isopropenyl acetate and 1 g of p-toluenesulfonic acid while the acetone formed is distilled off continuously. After cooling to room temperature, the excess isopropenyl acetate is distilled off, and the residue is shaken with 500 ml of tert-butyl methyl ether and 250 ml of water. The organic phase is dried using sodium sulfate and evaporated, and the residue is distilled under reduced pressure. The 6-chloro-3,4-dihydronaphthalen-1-yl acetate obtained in this way is stirred for 4 h at 100° C. together with an equimolar amount of methoxytributylstannane, during which the methyl acetate formed is continuously removed. The 6-chloro-3,4-dihydro-1-tributylstannyloxynaphthalene obtained after distillation under reduced pressure is dissolved in benzene together with the equivalent amount of ethyl bromoacetate and 0.25 times the molar amount of azobisisobutyronitrile, and the mixture is refluxed for 5 h. The residue obtained after removal by distillation is subjected to purification by column chromatography (silica gel 60 from Merck KGaA, Darmstadt, eluent toluene/isopropanol mixture, volume ratio 9:1). The 6-chloro-2-ethoxycarbonyl-1-tetralone obtained after removal of the solvent is stirred for 5 h at room temperature in ethanol with an excess of NaBH4. Dilute hydrochloric acid is then carefully added. The 6-chloro-2-ethoxycarbonyl-1-hydroxytetralin formed is extracted with diethyl ether. After drying using sodium sulfate, the organic phase is evaporated. The residue is again subjected to separation by column chromatography (conditions as mentioned above). The form with trans H atoms in the 1,2-position which arises as the principal fraction is converted into the benzyl ether using benzyl bromide in tetrahydrofuran with addition of NaH and (C4H9)4NI. After removal of the solvent, this benzyl ether is hydrolysed using alcoholic potassium hydroxide solution. After acidification using dilute hydrochloric acid, the carboxylic acid formed is purified by crystallisation from ethanol. After conversion into the carboxylic acid chloride using thionyl chloride, the diazomethyl ketone is prepared therefrom in a generally known manner by reaction with diazomethane. After addition of silver nitrate and ammonia, this diazomethyl ketone is rearranged to give the amide (Wolff rearrangement), which is hydrolysed using alcoholic potassium hydroxide solution. The carboxylic acid formed on acidification using dilute hydrochloric acid is filtered off with suction, dissolved in ethanol and hydrogenated after addition of catalyst (5% Pd on carbon). The σ-lactone is obtained by heating the reaction product obtained after removal of the catalyst by filtration and removal of the solvent by distillation to 100 to 140° C. This σ-lactone is allylated in tetrahydrofuran using lithium diisopropylamide and allyl bromide. 2-Allyl-7-chloro-4-oxa-1,2,3,4,4a,9,10,10a-octahydrophenanthrene is prepared therefrom in a generally known manner by reaction with LiAlH4 and boron trifluoride etherate (cf. G. R. Pettit et al. J. Org. Chem. 26, 4773 (1961)). Hydrogenation in tetrahydrofuran and addition of palladium/carbon (5% Pd) under atmospheric pressure gives 7-chloro-4-oxa-2-propyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene.