Beilstein J. Org. Chem.2012,8, 1695–1699, doi:10.3762/bjoc.8.192
Krystal A. D. Kamanos Jonathan M. Withey Department of Physical Sciences, Grant MacEwan University, 10700 104 Ave, Edmonton, T5J 4S2, Canada 10.3762/bjoc.8.192 Abstract A route is described for the enantioselective synthesis of (R)-(−)-complanine, a marine natural product isolated from Eurythoe
complanata, and known to be a causative agent in inflammation. An organocatalytic, asymmetric oxyamination of a homoconjugated all-Z-dienal intermediate provides versatile and efficient access to the natural product.
Keywords: complanine; enantioselective synthesis; marine fireworm; nitrosoaldol
; organocatalysis; Introduction
The marine fireworm Eurythoe complanata resides in the shallow water and sands of temperate and sub-tropical regions. Its small setae cause skin inflammation upon contact, the causative agent having been identified as complanine. This novel amphipathic substance was first isolated
Beilstein J. Org. Chem.2009,5, No. 12, doi:10.3762/bjoc.5.12
Kazuhiko Nakamura Yu Tachikawa Daisuke Uemura Department of Biosciences and Informatics, Keio University 3-14-1 Hiyoshi Yokohama 223-8622, Japan Graduate School of Science, Nagoya University Furo-cho Chikusa Nagoya 464-8566, Japan 10.3762/bjoc.5.12 Abstract The synthesis of (−)-complanine, an
inflammatory substance of Eurythoe complanata, was accomplished by a “chiral synthon” approach. The absolute configuration of this molecule was determined to be R.
Keywords: chiral synthon; complanine; inflammatory substance; marine fireworm; total synthesis; Introduction
Toxic marine annelids were first
actual toxic substance of these animals has remained unknown. We recently isolated a novel amphipathic substance, named complanine (Figure 1), from an amphinomid polychaete, Eurythoe complanata (Figure 2). Complanine has been identified as an inflammatory substance by bioassay-guided separations; and the