Facile total synthesis of the (-)-Heliconol A

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. (c) 2007 Elsevier Ltd. All rights reserved.