259187-17-2

Upstream product

• 117935-56-5 R-(+)-2-(hydroxymethyl)-4-pentenyl acetate 
• 3587-60-8 Benzyloxymethyl chloride 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 259187-18-3 3-benzyloxymethoxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-butan-1-ol 
• 259187-28-5 (2-benzyloxymethoxymethyl-4-iodo-butoxy)-tert-butyl-dimethyl-silane 
• 259187-30-9 (S)-6-[(R)-4-Benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-pentyl]-2,2,6-trimethyl-tetrahydro-pyran-3-ol 
• 259187-23-0 (S)-6-[(R)-4-Benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-pentanoyl]-2,2,6-trimethyl-dihydro-pyran-3-one 
• 259187-22-9 Benzoic acid (S)-6-[(R)-4-benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-pentyl]-2,2,6-trimethyl-tetrahydro-pyran-3-yl ester 

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.