67858-91-7

Upstream product

• 764-32-9 5-methyl-4-hexenal 
• 115-18-4 2-methyl-3-buten-2-ol 
• 556-82-1 3-methyl-2-buten-1-ol 
• 67859-01-2 6-methanesulfonyloxy-2-methyl-hex-2-ene 
• 42272-94-6 5-methylhex-4-ene-1-ol 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 42272-93-5 ethyl 5-methyl-4-hexenoate 
• 22539-80-6 diethyl (3-methylbut-2-enyl)malonate 
• 63588-94-3 6-iodo-2-methylhex-2-ene 
• 603-35-0 triphenylphosphine 

Downstream Products

• 110207-82-4 1,5-dimethyl-hex-4-enyl triphenyl phosphonium iodide 
• 473313-02-9 (6Z,10E)-12-tert-butyldimethylsilyloxy-6-tert-butyldiphenylsilyloxymethyl-2,10-dimethyl-2,6,10-dodecatriene 
• 76936-19-1 (1,5-Dimethyl-4-hexenylidene)-triphenylphosphorane 

Relevant academic research and scientific papers

Biosynthesis of (+)-epicubenol

Incubation of [6-2H]FPP (14a) with epicubenol synthase isolated from Streptomyces sp. LL-B7 gave epicubenol (1c) labeled at D-9 as established by 2H NMR. These results confirm the involvement of a predicted 1,2-hydride shift in the mechanism of formation of 1.

Evolution of a Polyene Cyclization Cascade for the Total Synthesis of (?)-Cyclosmenospongine

We report a full account on the development of a unique cationic polyene cyclization for the total synthesis of the tetracyclic meroterpenoid (?)-cyclosmenospongine. A highly convergent three-component coupling strategy enabled rapid access to individual cyclization precursors that were tested for their reactivity. The successful transformation generates three rings and sets four consecutive stereocenters in a single operation proceeding in a highly efficient manner to give exclusively the trans-decalin framework. In addition, we found that the enol ether geometry and the relative configuration of C3 and C8 are crucial for the success of the polyene cyclization.