Synthesis of the alleged structure of sclerophytin A. The setting of two oxygen bridges within the fused cyclodecanol B ring is not Nature's Way.
[reaction: see text] The structure attributed to sclerophytin A, a cytotoxic soft coral metabolite, was synthesized in an enantioselective manner from (5S)-5-(d-menthyloxy)-2(5H)-furanone. The spectral properties and polarity of the synthetic product require that the structural assignment to the natural material be revised.
Paquette
L A
LA
Evans Chemical Laboratories, The Ohio State University, Columbus, Ohio 43210, USA. paquette.1@osu.edu
Moradei
O M
OM
Bernardelli
P
P
Lange
T
T
D001671:Biochemistry / Q000379:methods*; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure
D001952:Bridged-Ring Compounds; D005663:Furans; C412667:sclerophytin A