208192-99-8

Upstream product

• 4746-97-8 cyclohexanedione monoethylene ketal 
• 220045-98-7 8-(7-Methoxy-benzo[1,3]dioxol-5-yl)-1,4-dioxa-spiro[4.5]decan-8-ol 
• 208193-14-0 6-(1,4-Dioxa-spiro[4.5]dec-7-en-8-yl)-4-methoxy-benzo[1,3]dioxole 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 91511-83-0 5-bromo-7-methoxy-1,3-benzodioxol 
• 38790-07-7 5-bromo-3-methoxybenzene-1,2-diol 
• 5034-74-2 5-bromo-3-methoxysalicylaldehyde 
• 220046-00-4 6-(1,4-Dioxa-spiro[4.5]dec-8-yl)-4-methoxy-benzo[1,3]dioxole 

Downstream Products

• 208193-00-4 Triisopropyl-[(S)-4-(7-methoxy-benzo[1,3]dioxol-5-yl)-cyclohex-1-enyloxy]-silane 
• 208193-04-8 3-Chloro-benzoic acid (1R,2R,3R)-3-(7-methoxy-benzo[1,3]dioxol-5-yl)-2-methoxycarbonylamino-6-oxo-cyclohexyl ester 
• 208193-05-9 3-Chloro-benzoic acid (1S,2R,3R)-3-(7-methoxy-benzo[1,3]dioxol-5-yl)-2-methoxycarbonylamino-6-oxo-cyclohexyl ester 
• 208193-02-6 [(1R,6R)-6-(7-Methoxy-benzo[1,3]dioxol-5-yl)-3-triisopropylsilanyloxy-cyclohex-2-enyl]-carbamic acid methyl ester 
• 208193-07-1 C₃₂H₃₄ClNO₈SeSi 
• 208193-12-8 Acetic acid (1R,2S,3S,4S,5R,6R)-2,3,4-triacetoxy-6-(7-methoxy-benzo[1,3]dioxol-5-yl)-5-methoxycarbonylamino-cyclohexyl ester 
• 208193-06-0 C₂₉H₃₈ClNO₈Si₂ 
• 208193-03-7 3-Chloro-benzoic acid (1R,5R,6R)-5-(7-methoxy-benzo[1,3]dioxol-5-yl)-6-methoxycarbonylamino-2-triisopropylsilanyloxy-cyclohex-2-enyl ester 
• 208193-08-2 3-Chloro-benzoic acid (1S,5R,6R)-5-(7-methoxy-benzo[1,3]dioxol-5-yl)-6-methoxycarbonylamino-2-oxo-cyclohex-3-enyl ester 
• 208193-11-7 [(1R,2S,3S,4S,5R,6R)-2,3,4,5-Tetrahydroxy-6-(7-methoxy-benzo[1,3]dioxol-5-yl)-cyclohexyl]-carbamic acid methyl ester 

Relevant academic research and scientific papers

Application of the β-azidonation reaction to the synthesis of the antitumor alkaloid (+)-pancratistatin

o-Vanillin 21 was converted into 24 following literature procedures. Treatment of 24 with n-BuLi/THF followed by addition of 25 gave 26. Dehydration (POCL3/pyridine/DBU), hydrogenation and hydrolysis of 26 gave the ketone 29. Chirality was introduced by deprotonation of 29 with the lithium salt of (+)-bis(αmethylbenzyl)amine, followed by triisopropylsilyl trifluoromethanesulfonate to give 30 (95%). β-Azidonation of 30 with (PhiO)n/TMSN3 rapidly produced 31 (95%) as a mixture of trans- and cis- diastereomers in a 3.5:1 ratio. Reduction with LiAIH4 followed by methyl chloroformate/pyridine gave 32, which on treatment with MCPBA/CH2CL2/imidazole resulted in 33. Hydrolysis of 33 gave 34, which when exposed to KOBu(t)/HMPA at 90 °C resulted in 39. After conversion of 39 into enone 42, epoxidation with NaHCO3/H2O2/MeOH gave 43. Reduction of 43 with L-selectride followed by solvolysis with sodium benzoate in water gave 46, which was immediately acetylated to give 47. Lactam formation (Tf2O/DMAP) converted 47 into 48 and the regioisomer 49 (7:1). The mixture of 48 and 49 demethylated to give 50 and the acetate protecting groups removed to give (+)pancratistatin 1.