Enantioselective total synthesis of (R)-(−)-complanine

• Krystal A. D. Kamanos and
• Jonathan M. Withey

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

(−)-Complanine, an inflammatory substance of marine fireworm: a synthetic study

• Kazuhiko Nakamura,
• Yu Tachikawa and
• Daisuke Uemura

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