91526-99-7

Upstream product

• 91526-98-6 benzyl (4R,5R)-2,2-dimethyl-5-(2-methyl-1,3-dithian-2-ylmethyl)-1,3-dioxolan-4-ylmethyl ether 
• 109613-50-5 (R,R)-4-benzyloxy-2,3-bis(1-ethoxyethoxy)-1-butanol 
• 100-39-0 benzyl bromide 
• 78469-76-8 (2R,3R)-1-benzyloxy-3,4-epoxy-2-(1'-methoxy-1'-methylaethoxy)-butan 
• 109715-58-4 (4R)-3,4-(isopropylidenedioxy)tetrahydrofuran-2-ol 
• 109613-51-6 (R,R)-4-benzyloxy-2,3-bis(1-ethoxyethoxy)butyl methanesulfonate 
• 109613-52-7 (R,R)-4-benzyloxy-2,3-dihydroxybutyl methanesulfonate 
• 72229-13-1 (2R,3R)-1-benzyloxy-3,4-epoxy-2-butanol 
• 91526-97-5 (4S,5R)-5-benzyloxymethyl-4-bromomethyl-2,2-dimethyl-1,3-dioxolane 
• 37031-29-1 (+)-dimethyl-2,3-O-isopropylidene-D-tartrate 
• 73346-74-4 (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol 
• 78469-77-9 1-O-benzyl-2,3-O-isopropylidene-D-threitol 
• 114826-50-5 (4R,5S)-4-((benzyloxy)methyl)-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolane 
• 872831-93-1 (4R,5R)-4-(benzyloxymethyl)-5-(1,3-dithian-2-ylmethyl)-2,2-dimethyl-1,3-dioxolane 

Downstream Products

• 91527-00-3 (2S,4R,5R)-6-benzyloxy-4,5-isopropylidenedioxy-2-hexanol 
• 91603-58-6 (2R,4R,5R)-6-benzyloxy-4,5-isopropylidenedioxy-2-hexanol 
• 872831-88-4 (4S,5R)-2,2-Dimethyl-5-(2-oxo-propyl)-[1,3]dioxolane-4-carboxylic acid (2-benzyloxy-ethyl)-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-amide 

Relevant academic research and scientific papers

Asymmetric total synthesis of the 1-epi-aglycon of the cripowellins A and B

The unusual [5.3.2]-bicyclic structure of the insecticidal Amaryllidaceae alkaloids cripowellin A (1) and B (2) has been synthesized for the first time via a sequence of Sharpless dihydroxylation, ring-closing metathesis, and intramolecular Heck reaction. The asymmetric synthesis of the 1-epi-aglycon 82 proceeds with virtually complete diastereo- and enantioselectivity (de, ee ≥ 98%) in 13 steps and an overall yield of 5.6%. In addition, three alternative approaches toward the aglycon 3 are also described focusing on (1) the alkylation of the 2-benzazepinedithianes 35 and 36 with the electrophile 11, (2) a radical cyclization of the precursor (R/S,S,S)-39, and (3) an intramolecular arylation reaction of the aryl ketone 47.

Total synthesis of (+)-colletodiol from (S,S)-tartrate and (R)-3-hydroxybutanoate

The macrodiolide antibiotic (+)-colletodiol (7, Scheme 1) was synthesised.The configuration was thus proven to be (6R,11R,12R,14R). - Key intermediates (Schemes 9 and 10) are the two hydroxy acids 43 and 64, which were prepared from dimethyl (S,S)-tartrate in 20percent overall yield (12 steps) and from (R)-3-hydroxybutanoate in 57percent overall yield (6 steps), respectively.The two hydroxy acids were cyclised to give, after deprotection, the title compound. - Our investigations led to the production of a large number of chiral building blocks, many of them in different stereoisomeric forms.

(+)-COLLETODIOL SYNTHESIS FROM (S,S)-TARTARIC ACID AND (R)-HYDROXY-BUTYRIC ACID

E-(R)-5-Hydroxy-2-hexenoic acid (4) and the acetonide of E-(4R,5R,7R)-trihydroxy-2-octenoic acid (3) are joined to give, after deprotection, (+)-colletodiol (1).The syntheses of the two hydroxy-acids from poly-(R)-3-hydroxy-butenoate (PHB) and (-)-tartaric acid, respectively, are outlined.