290334-91-7

Upstream product

• 290334-83-7 Benzoic acid (R)-2-methanesulfonyloxy-2-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl ester 
• 290836-45-2 6-O-benzoyl-1,2:3,4-di-O-isopropylidene-D-mannitol 
• 290334-90-6 5-hydroxy-1,2:3,4-di-O-isopropylidenenonane 
• 3969-59-3 mannitol triacetonide 
• 38145-93-6 1,2:3,4-di-O-isopropylidene-D-mannitol 
• 85325-93-5 1,2-anhydro-3,4:5,6-di-O-isopropylidene-D-glucitol 
• 290334-84-8 5-benzyloxy-1,2:3,4-di-O-isopropylidenenonane 

Downstream Products

• 290334-86-0 4-(1-benzyloxypentyl)-2,2-dimethyl-5-oxiranyl[1,3]dioxolane 
• 290334-87-1 1-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]pent-4-en-1-ol 
• 290334-88-2 6-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]tetrahydropyran-2-one 
• 290334-92-8 1-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]pentane-1,5-diol 
• 540727-82-0 3-benzenesulfonyl-1-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]-5-(tert-butyldimethylsilanyloxy)pentan-1-ol 
• 445396-71-4 (E)-3-[(4R,5R)-5-((S)-1-Benzyloxy-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acrylic acid ethyl ester 
• 445396-72-5 (R)-5-((1R,2S)-2-Benzyloxy-1-hydroxy-hexyl)-5H-furan-2-one 
• 290334-85-9 Toluene-4-sulfonic acid (R)-2-[(4R,5R)-5-((S)-1-benzyloxy-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl ester 

Relevant academic research and scientific papers

Total synthesis of (+)-boronolide, (+)-deacetylboronolide, and (+)-dideacetylboronolide

Total synthesis of (+)-boronolide, (+)-deacetylboronolide, and (+)-dideacetylboronolide has been achieved from a single intermediate 26, which was synthesized in 11 steps from a D-mannitol-derived intermediate 8 in an overall yield of 10%. The key steps in the synthesis are inversion of a chiral center by taking an advantage of the inherent mechanism involved in the ring closing to an epoxide via intramolecular SN2 reaction and lactonization of a diol using Fetizons reagent. The strategy is amenable to preparation of analogues of (+)-boronolide in sufficient amount for further screening of biological activity.

Formal total synthesis of (+)-boronolide

(+)-Boronolide, a polyacetoxy natural product having four contiguous asymmetric centers has been synthesized from D-mannitol. (C) 2000 Elsevier Science Ltd.