Process for the preparation of a bicyclic decalin ketone

Details Process for the preparation of a bicyclic decalin ketone Process for the preparation of a bicyclic decalin ketone

1993-07-20

1995-01-31

Reamer, James H.

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

C07C 4565

Patent

active

053860390

ABSTRACT:
Perhydro-5,5-8a-trimethyl-2-naphthalenone is prepared by acid cyclization of carboxylic esters of formula ##STR1## having a double bond in one of the positions indicated by the dotted lines and wherein symbol R designates a C.sub.1 -C.sub.6 alkyl radical, X stands for a monovalent radical of formula P(O)(OR.sup.1).sub.2 or C(O)R.sup.2, R.sup.1 represents a C.sub.1 -C.sub.6 alkyl group and R.sup.2 is either a linear or branched alkyl group or a substituted or unsubstituted phenyl radical, and wherein the wavy line represents a C--C bond of cis or trans configuration, or of formula ##STR2## wherein the wavy lines and symbol R are defined as above, and R.sup.0 represents a C.sub.3 -C.sub.6 alkyl radical, preferably branched, followed by basic decarboxylation of the obtained product.

REFERENCES:
patent: 3928246 (1975-12-01), Stadler et al.
patent: 3989739 (1976-11-01), Eschenmoser et al.
patent: 4007211 (1977-02-01), Trost et al.
S. Harring et al., "Terminator Regulated Mechanistic Divergence in BF.sub.3 .multidot.MeNO.sub.2 Promoted Cascade Annulations of Geometrically Defined Trienoate Derivatives", J. Chem. Commun., pp. 503-505 (1992).
G. Buchi et al., "The Synthesis of Recemic Abrox.RTM."; Helvetica Chimica Acta, 72:8, pp. 996-1000 (1989).

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