13 BEETA ARUKIRU 44 GON 3177 JIONNOSEIHO

Novel process for the preparation of 13 beta -alkyl-4-gonene-3,17-diones of the formula wherein R1 is methyl or ethyl, consists of REACTING A 7A beta -ALKYL,5,6,7,7A-TETRAHYDROINDANE-1,5-DIONE WITH FORMALDEHYDE AND AN ARYLSULFINIC ACID OR AN ADDUCT OF FORMALDEHYDE AND ARYLSULFINIC ACID TO PRODUCE A TETRAHYDROINDANE DERIVATIVE; HYDROGENATING THE TETRAHYDROINDANE DERIVATIVE WITH HYDROGEN IN THE PRESENCE OF A PALLADIUM-, PLATINUM-, OR RHODIUM-CONTAINING HYDROGENATION CATALYST TO PRODUCE A PERHYDROINDANE DERIVATIVE; CONDENSING THE PERHYDROINDANE DERIVATIVE IN THE PRESENCE OF A PROTON-ACCEPTING AGENT WITH A 7,7-ALKYLENEDIOXY-3-OXOOCTANOIC ACID ESTER; TREATING THE PRODUCT OBTAINED WITH A STRONG AQUEOUS BASE AND THEN HEATING THE PRODUCT IN AN INERT SOLVENT TO PRODUCE A 4,5-SECOSTEROID; HYDROGENATING THE 4,5-SECOSTEROID IN THE PRESENCE OF A PALLADIUM-, PLATINUM-, RHODIUM-, OR NICKEL-CONTAINING HYDROGENATION CATALYST; AND HYDROLYZING AND CYCLIZING THE HYDROGENATED 4,5-SECOSTEROID BY TREATMENT WITH A STRONG ACID.