112440-73-0

Upstream product

• 112440-64-9 (R)-(+)-3-(tert-butyldimethylsiloxy)-6-heptenal 
• 112440-68-3 (E)-(R)-1-(4-Methyl-furan-2-yl)-hepta-1,6-dien-3-ol 
• 112440-76-3 (R)-(-)-3-(tert-butyldimethylsiloxy)hept-6-enoate 
• 112440-69-4 (R)-1-<2-(4-methylfuryl)>-3-(2-propynyloxy)-1(E),6-heptadiene 
• 112440-65-0 (3R)-1-hydroxy-1-<2-(4-methylfuryl)>-3-(tert-butyldimethylsiloxy)-6-heptene 
• 112440-67-2 (3R)-1-<2-(4-methylfuryl)>-3-(tert-butyldimethylsiloxy)-1(E),6-heptadiene 
• 112440-72-9 (R)-7-But-3-enyl-3-methyl-4,4a,5,7,7a,8-hexahydro-benzo[1,2-b;4,5-c']difuran-5-ol 
• 112440-70-7 (7R)-3-methyl-7-(3-butenyl)-4,7,7a,8-tetrahydro-1,6-dioxa-s-indacene 
• 82065-64-3 methyl (R)-(-)-3-hydroxyhept-6-enoate 
• 17605-06-0 ethyl 3-oxohept-6-enoate 

Relevant academic research and scientific papers

Total Synthesis of (+)-4-Oxo-5,6,9,10-tetrahydro-4,5-secofuranoeremophilane-5,1-carbolactone via Novel Lactone Construction through Allene Intramolecular Cycloaddition

The first asymmetric synthesis of the title compound 1 is described.The crucial step is a facile construcion of the tricyclic lactone, the basic skeleton of 1, via allene intramolecular cycloaddition.Methyl (R)-(-)-3-hydroxyhept-6-enoate (3) was converted into the (R)-propargyl ether 8 in six steps.Base treatment (t-BuOK/t-BuOH, 83 deg C) of 8 caused a smooth cyclization via the intermolecular Diels-Alder reaction of the allenyl ether intermediate to give 9, which on successive hydration and oxidation provided the lactone 10 as a mixture of diastereomers.Aromatization of 10 afforded a single product (11), which was subjected to the Wacker oxidation to give (R)-(+)-1.