Results of a chiral approach to the gibbane frameworks are presented. Cyclization of the meso triketone(10), obtained through Michael reaction of 2-propargyl-1,3-indandione(14) with methyl vinyl ketone, using L-proline as chiral catalyst gave the chiral enone(8) via the chiral ketol(17). The enone(8) afforded the following gibbane frameworks, 24 by the ene reaction, and 20, 21 and 22 by acid catalyzed aldol type condensation via the acetyl intermediate (19). Similarly, the chiral gibbane frameworks, and 26, 27, and 29, were obtained from the allyl analogue(11) of 10. The propargyl enone(8) was transformed into the gibberic acid framework via the monoketal(36) and the ketenedithioacetal(38) intermediates.