259187-22-9

Upstream product

• 259187-21-8 Benzoic acid (S)-6-formyl-2,2,6-trimethyl-tetrahydro-pyran-3-yl ester 
• 259187-28-5 (2-benzyloxymethoxymethyl-4-iodo-butoxy)-tert-butyl-dimethyl-silane 
• 259187-20-7 Benzoic acid (S)-6-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-2,2,6-trimethyl-tetrahydro-pyran-3-yl ester 
• 259187-19-4 Benzoic acid 1-{2-[(2R,3R)-3-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-oxiranyl]-ethyl}-2-hydroxy-2-methyl-propyl ester 
• 259187-18-3 3-benzyloxymethoxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-butan-1-ol 
• 259187-17-2 (2-benzyloxymethoxymethyl-pent-4-enyloxy)-tert-butyl-dimethyl-silane 
• 65-85-0 benzoic acid 
• 117935-56-5 R-(+)-2-(hydroxymethyl)-4-pentenyl acetate 
• 50727-94-1 (2R,3R)-3-methyl-3-(4-methyl-3-pentenyl)oxiranemethanol 
• 3587-60-8 Benzyloxymethyl chloride 

Downstream Products

• 259187-23-0 (S)-6-[(R)-4-Benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-pentanoyl]-2,2,6-trimethyl-dihydro-pyran-3-one 
• 259187-30-9 (S)-6-[(R)-4-Benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-pentyl]-2,2,6-trimethyl-tetrahydro-pyran-3-ol 

Relevant academic research and scientific papers

Total synthesis of (+)-saponaceolide B

Coupling of three fragments results in the first total synthesis of a saponaceolide (see scheme). The first fragment, the spiroketal portion, is formed from two moieties, one derived from geraniol and the other from allyl malonate. A sulfone alkylation-desulfonylation sequence joins the spiroketal portion to the methylene-3,3-dimethylcyclohexane unit. The subsequent stereoselective Wittig reaction attaches the final piece to complete the synthesis of saponaceolide B (1), one of the most biologically active members of this family.