877762-62-4

Upstream product

• 54340-70-4 ethyl (E)-4-heptenoic acid ester 
• 97101-23-0 (4R,5R)-(-)-hydroxy-5 heptanolide-4 
• 865487-10-1 (4R,5R)-5-(t-butyldiphenylsolyloxy)-4-heptanolide 
• 106-95-6 allyl bromide 

Downstream Products

• 877762-71-5 (2S,4R,5S)-2-allyl-5-(p-nitrobenzoyloxy)-4-heptanolide 
• 877762-64-6 (2S,4R,5R)-2-[3-(t-butoxycarbonyl)-2-propenyl]-5-(t-butyldiphenylsilyloxy)-4-heptanolide 
• 877762-65-7 (E)-4-{(3S,5R)-5-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2-hydroxy-tetrahydro-furan-3-yl}-but-2-enoic acid tert-butyl ester 
• 865487-12-3 ethyl 4-{(3S,5R)-5-[(S)-1-(p-nitrobenzoyloxy)propyl]tetrahydrofuran-3-yl}-2-butenoate 
• 865487-11-2 (S)-1-[(2R,4S)-4-allyltetrahydrofuran-2-yl]propyl p-nitrobenzoate 
• 865487-09-8 (S)-1-[(2R,4R)-4-(2-oxoethyl)tetrahydrofuran-2-yl]propyl p-nitrobenzoate 
• 877762-63-5 {(3R,5R)-5-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2-oxo-tetrahydro-furan-3-yl}-acetaldehyde 

Relevant academic research and scientific papers

Enantioselective synthesis and stereochemical revision of communiols A-C, antibacterial 2,4-disubstituted tetrahydrofurans from the coprophilous fungus Podospora communis

The enantioselective synthesis of the originally proposed structure of communiol C, an antibacterial 2,4-disubstituted tetrahydrofuran natural product from the coprophilous fungus Podospora communis, and its epimer via the Sharpless asymmetric dihydroxylation as the source of chirality led us to propose that the genuine stereochemistry of communiol C should be 3R, 5R, and 6S. The synthesis of the (3R,5R,6S)-isomer of communiol C and its good accordance with natural communiol C in every respect enabled us to confirm the newly proposed (3R,5R,6S)-stereochemistry for communiol C. The stereochemistries of structurally-related natural products (communiols A and B) of the same microbial origin were also revised through their total synthesis.

Stereochemical revision of communiols D and H through synthesis

Based on the previously revised stereochemistries for communiols A-C, the ent-8-epi- and ent-6-epi-stereoisomers of the original structures proposed for communiols D and H, respectively, were synthesized as highly probable candidates for their genuine str

Enantioselective synthesis and stereochemical revision of communiols A-C

Enantioselective synthesis of the proposed structure of communiol C, an antibacterial tetrahydrofuran derivative produced by Podospora communis, and its stereoisomers revealed that the genuine stereochemistry of communiol C should be 3R, 5R, and 6S. Two o