1316735-67-7

Upstream product

• 6485-40-1 (R)-Carvone 
• 1298087-05-4 (1R,2R,4R,6R)-1-methyl-2-(2-(phenylthio)ethynyl)-4-(prop-1-en-2-yl)-7-oxa-bicyclo[4.1.0] heptan-2-ol 
• 766-77-8 Dimethylphenylsilane 

Downstream Products

• 1298087-20-3 (1R,2R,4R,6R)-1-methyl-6-((Z)-2-(dimethyl(phenyl)silyl)-2-(phenylsulfonyl)vinyl)-4-(prop-1-en-2-yl)-7-oxa-bicyclo[4.1.0]heptan-2-ol 
• 1298087-06-5 (1R,2R,4R,6R)-1-methyl-2-((Z)-2-(dimethyl(phenyl)silyl)-2-(phenylsulfonyl)vinyl)-4-(prop-1-en-2-yl)-7-oxa-bicyclo[4.1.0]heptan-2-ol 
• 1298087-07-6 (1R,2R,4R,6R)-1-methyl-2-((2R)-1-(dimethyl(phenyl)silyl)-4-(trimethylsilyl)-1-(phenylsulfonyl)but-3-yn-2-yl)-4-(prop-1-en-2-yl)-7-oxa-bicyclo[4.1.0]heptan-2-ol 
• 1298087-09-8 C₃₁H₄₂O₄SSi₂ 
• 1298087-10-1 (1R,3R,5R,6S,7S,8R)-8-ethynyl-6-methyl-7-(phenylsulfonyl)-3-(prop-1-en-2-yl)bi cyclo [4.2.0]octane-1,5-diol 
• 1298087-11-2 C₃₈H₄₅NO₇SSi₂ 

Relevant academic research and scientific papers

Synthesis of bicyclo[4.2.0]octan-2-ol, a substructure of solanoeclepin A

A sesterterpenoid solanoeclepin A (1) has a unique structure including a bicyclo[4.2.0]octane substructure, for which a new synthetic methodology is explored particularly to cyclize functionalized cyclobutane rings. An optically active (R)-carvone and a racemic cyclohexenone were each converted into the respective epoxyvinylsulfones, and then subjected to the heteroatom-directed conjugate addition (HADCA) by a lithium acetylide nucleophile. The intermediate carbanions from HADCA were used for the following epoxide opening reaction yielding the four-membered carbocyclic products.