An Expedient Synthesis of a Functionalized Core Structure of Bielschowskysin

摘要

Bielschowskysin (1, Scheme 1a) is a recently discovered marine natural product that possesses a novel molecular architecture and impressive biological properties. Isolated from the Caribbean gorgonian octocoral Pseudopterogorgia kallos and characterized by spectroscopic and X-ray crystallo-graphic analysis, bielschowskysin boasts an unprecedentedtricyclo9.3.0.0tetradecane ring system (see 2, Scheme 1 a) decorated with a large number of oxygen-containing functional groups and with 11 stereogenic centers. Its biological properties include antimalarial activity against Plasmodium falciparum (IC_(50) = 10 μg mL~(-1)) and potent and selective cytotoxicity against EKVX nonsmall lung cancer cells (GI_(50) < 10 nM) and CAKI-1 renal cancer cells (GI_(50) = 510 nM).