A convenient and general approach for cyclopenta[b]naphthalene derivatives containing a structurally diverse functionality at C-4 position has been successfully developed, whereby manganese(III) acetate plays a key role to facilitate the tandem 5-exo-dig and 6-exo/endo cyclization in an efficient manner. Various functional groups, including trimethyl silyl, aryl, ester, ketone, secondary/tertiary amide, phosphonate and halogen, capped on the terminal acetylenic unit are well tolerated under optimal reaction conditions. It is highly conceivable that this novel [6.6.5] framework formation procedure may have broad synthetic utility in light of its operational simplicity and high yields.
Date:
2014-10
Relation:
Advanced Synthesis and Catalysis. 2014 Oct;356(14-15):3025-3038.
