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2005
Other bioactive products
U 1300
Asymmetric Synthesis of the Stereoisomers of 11,12,15(S)-TrihydroxyeicosaAcid, a Potent Endothelium-Derived Vasodilator. —
03- 213 -5(Z),8(Z),13(E)-trienoic
The concise, asymmetric synthesis of all four stereoisomers of the title acid is carried
out. The triply convergent strategy highlights two procedures: i) the preparation and
stereospecific, copper-mediated cross-coupling of chiral α,β-dialkoxystannanes, e.g.
(IX), with organic electrophile (X), and ii) the utility of dialkylthionocarbamate as
orthogonal alcohol protecting group. The absolute configuration of the title acid is
established by agreement of its structure with that of (XVI). An in vitro bioassay of
(XVI) is comparable to that of the parent. — (FALCK*, J. R.; BARMA, D. K.;
MOHAPATRA, S.; BANDYOPADHYAY, A.; REDDY, K. M.; QI, J.; CAMPBELL,
W. B.; Bioorg. Med. Chem. Lett. 14 (2004) 19, 4987-4990; Dep. Biochem., Univ.
Tex. Southwest. Med. Cent., Dallas, TX 75390, USA; Eng.) — H. Hoennerscheid
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