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Short Paper | Regular issue | Vol 83, No. 11, 2011, pp.2627-2633
Published online, 6th October, 2011
DOI: 10.3987/COM-11-12340
A New Synthetic Approach to Pentacyclic Ring, 6,7,14,15-Tetrahydro[1,5]diazocino[1,2-a:6,5-a’]-8-dihydrodiindole

Kittisak Sripha,* Darius Paul Zlotos, UIrike Holzgrabe, and Somsak Ruchirawat

*Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Mahidol University, 447, Sri-Ayudhya Rd. Rachatevee, Bangkok 10400, Thailand

Abstract

The construction of a new pentacyclic ring system, 6,7,14,15-tetrahydro[1,5]diazocino[1,2-a:6,5-a]-8-dihydrodiindole (7) from simple precursors through our new synthetic route was presented to be a facile and concise method for an intramolecular N-alkylation of tosylate 12 which was obtained from N-acylation of indoline 4 with indole acid 9, followed by reduction and tosylation. This new synthetic approach can overcome the disadvantage of uncontrollable intermolecular double N-alkylation of the precursor 3 to produce the unexpected ring system 2.