194931-07-2

Upstream product

• 51849-22-0 iodomethyl phenyl sulfide 
• 98-59-9 p-toluenesulfonyl chloride 
• 194931-06-1 (1S,4R,7aS)-4,7a-Dimethyl-4-phenylsulfanylmethyl-2,4,5,6,7,7a-hexahydro-1H-inden-1-ol 
• 7205-91-6 phenylthiomethyl chloride 

Downstream Products

• 213690-29-0 C₂₁H₃₀N₂O₃S 
• 213689-83-9 Acetic acid ((4R,7aR)-4,7a-dimethyl-5,6,7,7a-tetrahydro-4H-inden-4-yl)-phenylsulfanyl-methyl ester 
• 213689-69-1 (3aR,7R)-3a,7-Dimethyl-7-phenylsulfanylmethyl-4,5,6,7-tetrahydro-3aH-indene 

Relevant academic research and scientific papers

The enantioselective total synthesis of (-)-myltaylenol

The unusual sesquiterpenoid alcohol (-)-myltaylenol (1) is synthesized by an intramolecular [4+2] cycloaddition of a chiral diene accessible from Hajos-Wiechert ketone by a sequence of reactions including stereoselective alkylation of an unsaturated ketone with thiophenylmethyl iodide as alkylation agent. As the link between diene and olefin a sulfonic ester group is used. The link permits control of the stereoselectivity of the [4+2] cycloaddition. After this key step the sulfonic ester group can be removed under oxidative conditions by molecular oxygen as oxidation agent, leading directly to a hydroxyketone that can be converted to (-)-myltaylenol by successive Shapiro reaction, regioselective hydroboration and Wittig reaction.

The enantioselective total synthesis of (-)-myltaylenol

Using an intramolecular Diels-Alder cycloaddition followed by an oxidative rupture of the connective unit as the key step, the unusual carbon framework of (-)-myltaylenol was established.