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Paper | Special issue | Vol 80, No. 1, 2010, pp.395-408
Published online, 14th July, 2009
DOI: 10.3987/COM-09-S(S)36
Synthesis of (+)-Batzelladine K

Miyuki Sekine, Yumi Iijima, Osamu Iwamoto, and Kazuo Nagasawa*

*Institute of Symbiotic Science and Technology, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei, Tokyo 184-8588, Japan

Abstract

Total synthesis of batzelladine K (1), a marine guanidine alkaloid, was achieved based upon successive 1,3-dipolar cycloaddition reaction of cyclic nitrone. The relative and absolute stereochemistry of 1 was established by spectral comparison of the natural and synthetic products and the trans-isomer, which was also synthesized.