1242430-86-9

Upstream product

• 1242430-85-8 (3R,5S)-5-(2,5-dimethoxy-4-methylphenyl)-2-methylhept-6-ene-2,3-diol 
• 1242430-81-4 C₁₀H₁₆O₄ 
• 1242430-82-5 (R)-6-(2-hydroxypropan-2-yl)-5,6-dihydro-2H-pyran-2-one 
• 1242430-83-6 (4S,6R)-4-(2,5-dimethoxy-4-methylphenyl)-6-(2-hydroxypropan-2-yl)tetrahydro-2H-pyran-2-one 
• 1242430-84-7 (3R,5R)-3-(2,5-dimethoxy-4-methylphenyl)-6-methylheptane-1,5,6-triol 

Relevant academic research and scientific papers

Racemic and enantioselective total synthesis of heliespirones A & C

An account of the total synthesis of (±)-, (+)-heliespirone A and (±)-, (-)-heliespirone C is presented. In the first-generation total synthesis, we found rac-24a could be easily transformed to rac-heliespirones A & C in a biomimic way. Taking the disappointing diastereoselectivity of prenylation from 3 to 4, the nonselective dihydroxylation from 4 to 5 and the lenthy route in strategy A into account, we designed a different synthetic plan targeting a highly enantioselective, concise and protective-group free synthesis of heliespirones A & C. The palladium-catalyzed Michael addition and Sharpless AD played the key roles in the formation of optical lactone V, which could be easily transformed to compound I through two additional steps and the succedent operations were the same as those in the first-generation total synthesis. Our synthetic efforts indicated the bio-generation of heliespirones A & C from 24a should be a real process in nature.

Asymmetric total synthesis of ent-heliespirones A & C

A concise 8-step synthetic route toward ent-heliespirones A & C is described. This synthetic strategy features a highly diastereoselective palladium-catalyzed Michael addition to form 3,5-trans lactone and a final biomimetic intramolecular oxa-spirocyclization.