807346-05-0

Upstream product

• 807346-11-8 (3R,4S,5S)-4-[(E)-hept-1-enyl]-3-methyl-5-pentyldihydrofuran-2(3H)-one 
• 807346-07-2 (S,S)-bis(1-pentylprop-2-ynyloxy)diphenylsilane 
• 807346-08-3 (S,S)-bis(1-pentylprop-2-enyloxy)diphenylsilane 
• 807346-09-4 (s,S)-4,7-dipentyl-2,2-diphenyl-4,7-dihydro[1,3,2]dioxasilepine 
• 807346-10-7 (1S,2Z,4S)-1-pentyl-4-propanoyloxynon-2-enyl propanoate 
• 330847-87-5 (6S,7Z,9S)-tetradec-7-ene-6,9-diol 

Relevant academic research and scientific papers

A versatile stereoselective approach to paraconic acids

A versatile methodology has been developed for the independent stereochemical control in the construction of all the stereocenters of the γ-butyrolactone skeleton that are present in paraconic acids (1 and 2). The configuration of the γ-carbon came from an enantiopure alk-2-yne-1,4-diol. Stereoselective partial reduction to a (Z)- or (E)-alk-2-ene-1,4-diol (10) controlled the stereochemistry of the β-carbon whereas the α-carbon stereochemistry in 1 was partially selected by a (Z)- or (E)-enolate formation of the 1,4-dipropanoate derived from diol (10).

A straightforward synthesis of (-)-phaseolinic acid

A concise approach to (-)-phaseolinic acid starting from commercially available (S)-oct-1-yn-3-ol is disclosed. The key steps are a ring-closing metathesis reaction to prepare a C2-symmetrical allylic diol and its desymmetrization to a γ-butyrolactone by using an Ireland-Claisen rearrangement. The 2S,3S,4S configuration of the levogyre natural product has been confirmed.