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Paper | Regular issue | Vol 78, No. 8, 2009, pp.2041-2052
Published online, 17th April, 2009
DOI: 10.3987/COM-09-11716
Synthesis of Aryltetralin Type 2-Azalignans Using Schöllkopf ’s Bislactim-Ether Methodology

Yoshihide Usami,* Masao Arimoto,* Kiyomi Kobayashi, Mikiko Honjou, Masako Yamanaka, Misaki Miyao, Hayato Ichikawa, Kenneth F. Bastow, and Kuo-Hsiung Lee

*Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan


Synthesis of (1S,3R)-2-aza-4-deoxypodophyllotoxin has been accomplished in 6 steps using Schöllkopf’s bislactim-ether methodology in 12% total yield. Bislactim-ether, which was originally prepared from commercially available L-valine and glycine, was used as the starting material. Our synthetic route was allied to easy access to aryltetralin type 2-azalignan analogues. Synthesized 2-azalignans were tested for in vitro anticancer activity using a panel of human cancer cell lines. Both of two (1S)-diastereomers (9a and 9b) of 2-aza-4-deoxypodophyllotoxin showed significant activity against human cancer cell lines: A-549 (lung), HTC-8 (ileocecal), and MCF-7 (breast cancer).