862846-97-7

Upstream product

• 441004-47-3 (E)-1-(4-Iodo-furan-3-yl)-4-methyl-hex-4-en-1-one 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 27799-31-1 4-methyl-trans-4-hexenal 
• 862847-02-7 tert-Butyl-((4R,7R)-7-methyl-7-vinyl-4,5,6,7-tetrahydro-isobenzofuran-4-yloxy)-diphenyl-silane 
• 862846-96-6 (4R,7R)-7-Methyl-7-vinyl-4,5,6,7-tetrahydro-isobenzofuran-4-ol 
• 862847-03-8 2-[(4R,7R)-7-(tert-butyldiphenylsilanyloxy)-4-methyl-4,5,6,7-tetrahydroisobenzofuran-4-yl]ethanol 
• 627075-78-9 (E)-1-(4-Iodo-furan-3-yl)-4-methyl-hex-4-en-1-ol 

Downstream Products

• 923275-80-3 9-benzyloxy-8-isopropyl-10-methoxymethoxy-5a,7a-dimethyl-3,4,5,5a,6,7,7a,8,9,10,10a,10b-dodecahydro-2H-1-oxa-benzo[cd]cyclopenta[h]azulen-3-ol 
• 923275-75-6 9-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-8-isopropyl-5a,7a-dimethyl-3,4,5,5a,6,7,7a,8,9,10,10a,10b-dodecahydro-2H-1-oxa-benzo[cd]cyclopenta[h]azulen-10-ol 
• 923275-74-5 9-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-8-isopropyl-2-methoxy-5a,7a-dimethyl-2,3,4,5,5a,6,7,7a,8,9,10a,10b-dodecahydro-1-oxa-benzo[cd]cyclopenta[h]azulen-10-one 
• 923275-79-0 (9-benzyloxy-8-isopropyl-10-methoxymethoxy-5a,7a-dimethyl-3,4,5,5a,6,7,7a,8,9,10,10a,10b-dodecahydro-2H-1-oxa-benzo[cd]cyclopenta[h]azulen-3-yloxy)-tert-butyl-diphenyl-silane 
• 923275-73-4 4-{2-[4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-isopropyl-1-methyl-cyclopent-2-enyl]-ethyl}-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran 
• 862846-99-9 (4S,7R)-4-{2-[(1S,4R,5S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-isopropyl-1-methyl-cyclopent-2-enyl]-ethyl}-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran 
• 862847-00-5 (2R,3R,5aS,7aS,8S,9R,10aR,10bS)-9-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-8-isopropyl-2-methoxy-5a,7a-dimethyl-2,3,4,5,5a,6,7,7a,8,9,10a,10b-dodecahydro-1-oxa-benzo[cd]cyclopenta[h]azulen-10-one 
• 862846-98-8 (2R,3S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-{2-[(4S,7R)-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran-4-yl]-ethyl}-3-isopropyl-4-methyl-cyclopentanone 
• 923275-72-3 2-benzyloxy-4-{2-[7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran-4-yl]-ethyl}-3-isopropyl-4-methyl-cyclopentanone 

Relevant academic research and scientific papers

Total synthesis of (-)-heptemerone B and (-)-guanacastepene E

A concise, stereoselective, and convergent total synthesis of the unnatural enantiomer of the neodolastane diterpenoid heptemerone B has been completed. Saponification of (-)-heptemerone afforded (-)-guanacastepene E. The absolute stereochemistry of (-)-heptemerone B was thus established as 5-(S), the same as (-)-guanacastepene E. The longest linear sequence of the synthesis comprises 17 (18) steps from simple known starting materials. Our general synthetic approach integrates a diverse set of reactions, including an intramolecular Heck reaction to create one quaternary stereocenter and a cuprate conjugate addition for the establishment of the other. The central seven-membered ring was closed with an uncommon electrochemical oxidation, whereas the five-membered ring was formed through ring-closing metathesis. The absolute configuration of the two key building blocks was established through an asymmetric reduction and an asymmetric ene reaction.

An electrochemical approach to the guanacastepenes

(Chemical Equation Presented) An asymmetric approach toward the [6-7-5] ring system of the guanacastepenes is described.