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2005
Other bioactive products
U 1300
Synthesis of (-)-Tuliparin B Utilizing 2-Bromo-1-alkenes Conveniently Synthefrom the 3-O-Substituted 1,2-Dibromoalkane System by Regioselective
08- 241 sized
Elimination. — The synthesis of tuliparin B (VIII), having a variety of biological properties including cutaneous allergenic activity, proceeds via regioselective HBr elimination of the vicinal dibromide (IV). The regioselectivity and yield of the HBr eliminations is regulated by the strong electron-withdrawing effect of O-functional acyl groups
in (IV). The synthesis of the desired lactone (VIII) is accomplished by carbonylation
of the bromoalkene system (VI) using the safe and convenient dicarbonyl reagent (VII).
Starting from commercially available butenediol (I), the total yield of this route is 19%
for 5 steps, although the final step is not optimized. — (OHGIYA, T.; NISHIYAMA*,
S.; Heterocycles 63 (2004) 10, 2349-2354; Dep. Chem., Fac. Sci. Technol., Keio
Univ., Kohoku, Yokohama 223, Japan; Eng.) — H. Hoennerscheid
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