Citation: Wen-Bo Mu, Yue Zou, Quan-Rui Wang, Andreas Goeke. A novel synthetic route to rac-(Z)-recifeiolide from cyclooctanone and acetaldehyde[J]. Chinese Chemical Letters, ;2015, 26(11): 1393-1396. doi: 10.1016/j.cclet.2015.07.006 shu

A novel synthetic route to rac-(Z)-recifeiolide from cyclooctanone and acetaldehyde

Wen-Bo Mu ^a ,
Yue Zou ^b ,
Quan-Rui Wang ^a,, ,
Andreas Goeke ^b,,

1.
a Department of Chemistry, Fudan University, Shanghai 200433, China;
b Fragrance Ingredient Research Center, Givaudan Fragrances (Shanghai) Ltd.
b Fragrance Ingredient Research Center, Givaudan Fragrances (Shanghai) Ltd., Shanghai 201203, China

Corresponding author: Quan-Rui Wang, Andreas Goeke,
Received Date: 15 April 2015
Available Online: 16 June 2015

A novel synthetic approach to (±)-Z-recifeiolide 6, a 12-membered-ring lactone which can be selectively isomerized into (E)-recifeiolide, a natural antibiotic product isolated from fungus (Cephalosporium recifei) is reported. The synthesis is accomplished in five steps starting from readily available cyclooctanone and acetaldehyde based on the Lewis acid-catalyzed TMS-directed oxy-2-oxonia-Cope rearrangement. The work represents a novel strategy to assemble related macrolides.
- Synthesis
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