Facile total synthesis of the (−)-Heliconol A |
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| Authors: | Weiguo Quan Jiyong Zhang Xuegong She Xinfu Pan |
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| Affiliation: | a Department of Chemistry, State Key Lab of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, PR China
b State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, PR China |
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| Abstract: | The facile total synthesis of the (−)-Heliconol A (ent-1) as well as its diastereoisomer 18 is described, in which different reaction sequences lead to different results. The osmylation of 15 followed by hydrolysis afforded a single isomer 18, otherwise, a mixture of ent-1 and 18 resulted. Other important processes include the catalytic asymmetric CBS reduction and induced osmylation. The synthesis proceeded with a sequence of 11 steps, affording ent-1 in 9.0% and 18 in 22% overall yield, respectively. |
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