194656-83-2

Upstream product

• 1826-67-1 vinyl magnesium bromide 
• 166757-85-3 (R)-5-Benzyloxy-5-methyl-cyclohex-2-enone 
• 194656-80-9 (1R,5R)-1-Methyl-3-phenyl-2,4-dioxa-bicyclo[3.3.1]non-6-ene 
• 194656-76-3 C₁₀H₁₆O₄ 
• 166757-84-2 (1R,5R)-5-Benzyloxy-5-methyl-cyclohex-2-enol 
• 166757-81-9 (3aS,4R,6R,7aR)-2,2,6-Trimethyl-hexahydro-benzo[1,3]dioxole-4,6-diol 
• 166757-82-0 (1R,3R)-1-Methyl-cyclohex-4-ene-1,3-diol 
• 166757-80-8 ((3aR,5R,7R,7aS)-5,7-dihydroxy-2,2-dimethylhexahydro-1,3-benzodioxol-5-yl)methyl 4-methylbenzenesulfonate 
• 101917-46-8 (3aS,4R,6R,7aR)-6-Hydroxymethyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-4,6-diol 

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.