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

• 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

• 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

• , 127.6, 69.5, 65.5, 52.9 (3C), 45.9, 33.8, 31.7, 25.2, 23.3, 20.2, 18.8, 13.8. Synthesis of (S)-complanine, (S)-1: The enantiomer of natural complanine was also synthesized from (S)-malic acid. (S)-1 (ent-complanine): [α]D23 = 11.1 (c 0.65, H2O). Structure of (R)-(−)-complanine. Marine fireworm Eurythoe