137567-95-4

Upstream product

• 26054-46-6 (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 74-88-4 methyl iodide 
• 34638-25-0 (1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one 

Downstream Products

• 286408-54-6 (1R,3S,4S,5R,6S,7S)-3-methoxy-4,6-dimethyl-7-[4-methoxybenzyloxy]-2-oxabicyclo[3.3.0]-octane 
• 286408-56-8 (1R,2S,3S,4S)-2-(3R-butenyl)-4-[4-methoxy-benzyloxy]-3-methyl-cyclopentanol 
• 286408-57-9 (2S,3S,4S)-2-(3R-butenyl)-3-methyl-4-[4-methoxy-benzyloxy]-cyclopentanone 
• 286408-55-7 (1R,3RS,4S,5R,6S,7S)-4,6-dimethyl-7-[4-methoxy-benzyloxy]-2-oxabicyclo[3.3.0]-octane-3-ol 

Relevant academic research and scientific papers

Synthesis of the C1-C9 fragment of callipeltoside-A

(Equation presented) The C1-C9 fragment of callipeltoside (17) was prepared in 12 steps and 7.2% overall yield from bicyclic lactone (+)-4. Key steps include a stereoselective epoxidation and further regiocontrolled nucleophilic opening of the oxirane ring to install two vicinal stereocenters (C5 and C6), and the use of bis(trimethylsilyl) peroxide and a catalytic amount of Sn(IV) chloride for the chemoselective Baeyer-Villiger oxidation of unsaturated cyclopentanone 15.

SYNTHESIS OF NOVEL BICYCLIC ALCOHOLS AND THEIR NITRATES

1(R),5(S)-2-oxa-bicyclooct-6-en-3-one (2), a chiral by-product of the manufacture of prostaglandin derivatives, is easily converted into the alcohols (5a), (6a), (6c) and nitrates (5b), (6b), and (6d).Regio- and stereoisomers were identified on the basis of their NMR spectra.

Enzyme-catalysed Baeyer-Villiger Oxidations of Some Substituted Bicycloheptanones

The ketones 1 and 4 are oxidized to γ-lactones 2 and 5 with low enantioselectivity by both Acinetobacter sp.NCIB 9871 and Pseudomonas sp.NCIB 9872; in contrast the ketones 7 and 10 are biotransformed to products 8/9 and 11 respectively of very high optical purity.