Efficient Synthesis of (±)‐Juglomycin A

Unified Approach toward Syntheses of Juglomycins and Their Derivatives

“…); [α] D 28 −117 (c 0.01, MeOH); IR (KBr) ν max : 3338, 3167, 2972, 2926, 1670, 1641, 1614, 1454 cm −1 . 1 H NMR (400 MHz, CD 3 OD, TMS): δ 7.68 (dd, J = 8.0, 7.6 Hz, 1H), 7.62 (dd, J = 7.6, 0.8 Hz, 1H), 7.27 (dd, J = 8.0, 1.2 Hz, 1H), 6.93 (s, 1H), 4.27 (m, 1H), 2.82 (ddd, J = 13.6, 4.4, 1.2 Hz, 1H), 2.64 (dd, J = 13.6, 8.4 Hz, 1H), 2.43 (m, 2H); 13 (S)-3-(Methoxymethoxy)-4-{5′-(methoxymethoxy)-3′methyl-1′,4′-dioxo-1′,4′-dihydronaphthalen-2′-yl}butanoic Acid (16). CAN (139 mg, 0.254 mmol) was added to a solution of 10 (40.0 mg, 0.102 mmol) in a 1:1 mixture of MeCN and water (8 mL) at 0 °C.…”

“…14,15 Min and co-workers synthesized (±)- 1 from 1-hydroxy-5-methoxynaphthalene. 16 The Dötz benzannulation route to the enantioselective synthesis of (−)- and (+)- 1 has been reported by Fernandes and co-workers. 17−19 Both enantiomers of 3 and 4 were synthesized by the stereoselective aldol reaction of chiral sulfoxides with an aldehyde by our group.…”

“…The synthesis of (±)- 1 and (±)- 2 was reported by Giles and co-workers . Brimble and co-workers achieved the formal synthesis of (±)- 1 and (±)- 2 via oxidative fragmentation of furo­[3,2- b ]­naphtho­[2,1- d ]­furans. , The racemic and asymmetric synthesis of 1 using a reaction of a naphthol anion with a chiral aldehyde was reported by Kraus and co-workers. , Min and co-workers synthesized (±)- 1 from 1-hydroxy-5-methoxynaphthalene . The Dötz benzannulation route to the enantioselective synthesis of (−)- and (+)- 1 has been reported by Fernandes and co-workers. − Both enantiomers of 3 and 4 were synthesized by the stereoselective aldol reaction of chiral sulfoxides with an aldehyde by our group .…”

Discussion Addendum For:Ortho‐Formylations Of Phenols;Preparation Of 3‐Bromosalicylaldehyde

“…14b 5-Methoxy-2-naphthol was formylated in 75% yield as part of the total synthesis of racemic juglomycin A. 15 Oxygen functions are well tolerated; several mono protected resorcinols and methylenedioxy-substituted phenols have been formylated in excellent yields and high regioselectivity. 16,17 Moreover, several methylthioand phenylthiophenol derivatives have been formylated in high yields.…”