Investigations Directed Toward the Total Synthesis of Shionone

Author: Tilley, Jefferson Wright

Year: 1972

Degree: Dissertation (Ph.D.)

Advisor: Ireland, Robert E.

Committee Member: Unknown, Unknown

Option: Chemistry

DOI: 10.7907/em00-jn68

Abstract

An approach to the total synthesis of the tetracyclic triterpene shionone i is described. The key intermediate ii was prepared in 17 steps (3.0% overall yield) from 2-methyl- 1,3-cyclohexanedione. Generation of the essential trans, disubstituted C/D ring fusion of ii was accomplished via the stereospecific formation and cleavage of a fused methoxy- cyclopropane system. An additional 12 steps served to convert the ketone ii into the ketal-ketone iii (12.5%) which requires only addition of the side chain to complete the total synthesis.

See abstract in PDF for figures i,ii and iii

Files

• Tilley_JW_1971.pdf (application/pdf)