Perhydroindanone Derivatives. I. Applicability of the Diels-Alder

PERHYDROISDASONE DERIVATIVES. I

JANUARY, 1963

27

Perhydroindanone Derivatives. I. Applicability of the Diels-Alder Reactionla HERBERT 0. HOUSEBND

GARY

H. R A s M ~ ~ S O N ' ~

Department o j Chemastry, Jlassachusetts Institute of Technoloyy, Cambrzdge, Massachusetts Recezzetl July 1, 1962 The reactions summarized in Charts I and I1 have been carried out t o explore the use of the Diels-Alder reaction for the preparation of variousl?, substituted perhydroindanones.

I n anticipation of synthetic work directed toward the synthesis of the gibberellins,2we have investigated both the syntheses and chemical properties of a number of perhydroindanone systems i. Since we envision these systems, 1, to be models of the A-B ring system in the gibberellins, we have been particularly concerned with those derivatives which bear methyl and, or carboxyl substituents at position 7.

,a

1

Pd-C

4

0

I n this and the subsequent paper of this series, \ye have explored the possible utility of various cyclopentenones as dienophiles in the Diels-Alder reaction as well as the possible use of a 3-vinyl-2-cyclopenten-lone as a diene. This latter approach is summarized by the reactions outlined in Chart I which st