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Paper | Special issue | Vol 103, No. 2, 2021, pp.862-877
Published online, 8th February, 2021
DOI: 10.3987/COM-20-S(K)53
Divergent Total Synthesis of Azalamellarins D and N

Tsutomu Fukuda,* Seiya Okutani, Mayu Sumi, Kazuhito Miyagi, Gen Onodera, and Masanari Kimura

*Division of Chemistry and Materials Science, Graduate School of Engineering, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan

Abstract

Lamellarins are polycyclic marine alkaloids with potent cytotoxic activities against cancer cell lines. A divergent synthesis of azalamellarins D and N, lactam congeners of the marine natural products lamellarins D and N, has been achieved via the pentacyclic 14-bromo-8,9-dihydro-benzo[7,8]indolizino[3,2-c]- quinolin-6(5H)-one intermediate. The pentacyclic intermediate can be synthesized from methyl 1-(benzensulfonyl)-3-bromo-1H-pyrrole-2-carboxylate via the Suzuki–Miyaura cross-coupling and intramolecular direct arylation as key reactions.