121463-10-3Relevant academic research and scientific papers
The total synthesis of (±)-arisugacin A
Hsung, Richard P.,Cole, Kevin P.,Zehnder, Luke R.,Wang, Jiashi,Wei, Lin-Li,Yang, Xiao-Fang,Coverdale, Heather A.
, p. 311 - 324 (2003)
A 20-step total synthesis of (±)-arisugacin A with an overall yield of 2.1% is described here in detail. This synthesis features a formal [3+3] cycloaddition reaction of α,β-unsaturated iminium salts with 6-aryl-4-hydroxy-2-pyrones through a highly stereoselective 6π-electron electrocyclic ring-closure of 1-oxatriene. A strategic dihydroxylation-deoxygenation protocol leading to the desired angular C12a-OH was developed to serve as a critical step in leading to the final total syntheses of arisugacin A. This synthetic endeavor also led to an interesting and unexpected retro-aldol-aldol sequence in the AB-ring.
Total synthesis of forskolin - Part I
Delpech, Bernard,Calvo, Daniel,Lett, Robert
, p. 1015 - 1018 (2007/10/03)
A new total synthesis of forskolin 1 has been achieved and this note describes the synthesis of the transfused enone 18 as a key-intermediate. Key steps are: 1) the intramolecular Diels-Alder reaction of 17 to afford the tricyclic lactone 8 (48-56%); 2) a
AN APPROACH TO FORSKOLIN AN EFFICIENT SYNTHESIS OF A TRICYCLIC LACTONE INTERMEDIATE
Li, Tsung-Tee,Wu, Yu-Lin
, p. 4039 - 4040 (2007/10/02)
Tricyclic lactone l0, a potential intermediate for the synthesis of forskolin, was prepared from (+/-)-3-hydroxycyclocitral employing an intramolecular Michael addition as the key step.
