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; marinefireworm; nitrosoaldol
; organocatalysis; Introduction
The marinefireworm 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
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; marinefireworm; 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.
Marinefireworm Eurythoe