55784-75-3

Upstream product

• 57766-64-0 3-formamido-3,7,11,15-tetramethylhexadeca-1,6,10,14-tetraene 
• 154614-40-1 3-acetamido-3,7,11,15-tetramethylhexadeca-1,6,10,14-tetraene 
• 1295581-02-0 (S,E)-tert-butyl 4-(3-ethoxy-3-oxoprop-1-enyl)-2,2,4-trimethyloxazolidine-3-carboxylate 
• 1295581-18-8 (S)-tert-butyl 4-(3-ethoxy-3-oxopropyl)-2,2,4-trimethyloxazolidine-3-carboxylate 
• 1295581-03-1 (S,E)-tert-butyl 4-(5-ethoxy-4-methyl-5-oxopent-3-enyl)-2,2,4-trimethyloxazolidine-3-carboxylate 
• 1295581-19-9 C₁₇H₃₁NO₄ 
• 1295581-05-3 C₁₇H₃₀BrNO₃ 
• 1295581-06-4 C₃₃H₅₁NO₅S 
• 1295581-07-5 (S)-tert-butyl 2,2,4-trimethyl-4-((3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl)oxazolidine-3-carboxylate 
• 1295581-12-2 tert-butyl (S,5E,9E)-1-hydroxy-2,6,10,14-tetramethylpentadeca-5,9,13-trien-2-ylcarbamate 
• 1295580-96-9 tert-butyl (S,5E,9E)-2,6,10,14-tetramethyl-1-oxopentadeca-5,9,13-trien-2-ylcarbamate 
• 1295581-13-3 tert-butyl (S,6E,10E)-3,7,11,15-tetramethylhexadeca-1,6,10,14-tetraen-3-ylcarbamate 
• 1295581-20-2 N-((S,6E,10E)-3,7,11,15-tetramethylhexadeca-1,6,10,14-tetraen-3-yl)formamide 
• 24034-73-9 Geranylgeraniol 

Relevant academic research and scientific papers

Chirality Transfer from a Chiral Primary Alcohol Equivalent Through Allyl Cyanate-to-Isocyanate Rearrangement: Synthesis of (+)-Geranyllinaloisocyanide

A new approach was developed to construct quaternary stereogenic centers bearing nitrogen substituents in an enantioselective manner. The strategy takes advantage of [1,3]-chirality transfer from a chiral primary alcohol equivalent through an allyl cyanate-to-isocyanate rearrangement. This approach was employed in an efficient eight-step synthesis of the marine natural product, (+)-geranyllinaloisocyanide, in 43percent overall yield.

Asymmetric synthesis of (+)-geranyllinaloisocyanide: Assignment of absolute stereochemistry

The first nonracemic synthesis of (+)-geranyllinaloisocyanide, starting with (-)-lactic acid methyl ester, has been accomplished by exploiting a [3.3] sigmatropic rearrangement of allyl cyanate. The synthesis enables assignment of the S configuration of the C(3) isocyano substituted, quaternary stereogenic center in natural geranyllinaloisocyanide.

Novel, Regioselective Allylamine Construction; First Synthesis of Geranyllinaloisocyanide, a Diterpene from the Marine Sponge, Halichondria Sp.

The first synthesis of the diterpene, 3-isocyano-3,7,11,15-tetramethylhexadeca-1,6,10,14-tetraene (geranyllinaloisocyanide, 1), has been achieved through an allyl cyanate-to-isocyanate rearrangement.The crucial step in this synthesis is in situ transformation of allyl isocyanates into stable allyl acetamides with trimethylaluminium.