268736-74-9

Upstream product

• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 

Downstream Products

• 400737-16-8 (2S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxy)-4-methoxy-dec-8-yn-1-ol 
• 400737-13-5 tert-Butyl-((S)-1-{(S)-2-[(S)-2-(3,4-dimethoxy-phenyl)-[1,3]dioxolan-4-yl]-1-methoxy-ethyl}-hex-4-ynyloxy)-dimethyl-silane 
• 400736-32-5 (2S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxy)-4-methoxy-dec-8-ynal 

Relevant academic research and scientific papers

A new method for the preparation of non-terminal alkynes: Application to the total syntheses of tulearin A and C

Lactones are known to react with the reagent generated in situ from CCl4 and PPh3 in a Wittig-type fashion to give gem-dichloro-olefin derivatives. Such compounds are now shown to undergo reductive alkylation on treatment with organolithium reagents RLi to furnish acetylene derivatives bearing the substituent R at their termini (R=Me, n-, sec-, tert-alkyl, silyl); the reaction can be catalyzed with either Cu(acac)2 or Fe(acac)3/1,2-diaminobenzene. Two alkynol derivatives prepared in this way from readily accessible lactone precursors served as the key building blocks for the total syntheses of the cytotoxic marine macrolides tulearin A (1) and C (2). The assembly of these fragile targets hinged upon ring closing alkyne metathesis (RCAM) followed by a formal trans-reduction of the resulting cycloalkynes via trans-hydrosilylation/protodesilylation.