166757-92-2

Upstream product

• 166757-80-8 ((3aR,5R,7R,7aS)-5,7-dihydroxy-2,2-dimethylhexahydro-1,3-benzodioxol-5-yl)methyl 4-methylbenzenesulfonate 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 194656-80-9 (1R,5R)-1-Methyl-3-phenyl-2,4-dioxa-bicyclo[3.3.1]non-6-ene 
• 194656-76-3 C₁₀H₁₆O₄ 
• 166757-87-5 (1R,5R)-5-Benzyloxy-5-methyl-3-vinyl-cyclohex-2-enol 
• 166757-90-0 C₄₁H₄₆O₁₃ 
• 194656-96-7 Acetic acid 5-benzyloxy-2-((2R,4R,5R,6R)-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-naphthalen-1-yl ester 
• 166941-78-2 5-Benzyloxy-2-((2R,4R,5R,6R)-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-naphthalen-1-ol 
• 166757-88-6 5-acetoxy-6-(3,4-di-O-acetyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2-bromo-[1,4]naphthoquinone 
• 166757-94-4 Acetic acid 2-((2R,4R,5S,6R)-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-5-hydroxy-naphthalen-1-yl ester 
• 166757-86-4 (R)-5-Benzyloxy-5-methyl-3-vinyl-cyclohex-2-enone 
• 166757-84-2 (1R,5R)-5-Benzyloxy-5-methyl-cyclohex-2-enol 
• 166757-85-3 (R)-5-Benzyloxy-5-methyl-cyclohex-2-enone 
• 166757-81-9 (3aS,4R,6R,7aR)-2,2,6-Trimethyl-hexahydro-benzo[1,3]dioxole-4,6-diol 

Downstream Products

• 194656-97-8 Acetic acid (2R,3R,4R,6R)-3-acetoxy-6-((R)-3-benzyloxy-8-hydroxy-3-methyl-1,7,12-trioxo-1,2,3,4,7,12-hexahydro-benzo[a]anthracen-9-yl)-2-methyl-tetrahydro-pyran-4-yl ester 

Relevant academic research and scientific papers

A unified strategy for the total synthesis of the angucycline antibiotics SF 2315A, urdamycinone B, and the shunt metabolite 104-2

Total syntheses of the angucycline antibiotics SF 2315A (2), urdamycinone B (4), and the shunt metabolite 104-2 (5) are described, as well as an approach toward the synthesis of SF 2315B (3). All four syntheses feature a Diels-Alder cycloaddition between a bromojuglone derivative and an optically active diene (25a), the latter derived from (-)-quinic acid. Subsequent key transformations include (i) stereocontrolled introduction of ring fusion oxygen functionality featured in SF 2315A (2) and SF 2315 B (3), (ii) preparation of C-glycosyl juglone 53, and (iii) NMO mediated oxidative aromatization of 60.