1963
DOI: 10.1021/ja00898a048
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Stereospecific Total Synthesis of dl-Atisine

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Cited by 62 publications
(21 citation statements)
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“…The C 20 -diterpenoid alkaloids have also served as classic targets in natural product synthesis, resulting in the total syntheses of natural products within the atisine (1), [13][14][15][16][17][18] veatchine (5), [19][20][21][22][23] and napelline (6) [24,25] subclasses. Despite this progress, synthetic efforts toward the hetisine subclass (4) have been comparatively sparse.…”
Section: Introductionmentioning
confidence: 99%
“…The C 20 -diterpenoid alkaloids have also served as classic targets in natural product synthesis, resulting in the total syntheses of natural products within the atisine (1), [13][14][15][16][17][18] veatchine (5), [19][20][21][22][23] and napelline (6) [24,25] subclasses. Despite this progress, synthetic efforts toward the hetisine subclass (4) have been comparatively sparse.…”
Section: Introductionmentioning
confidence: 99%
“…[5] 1 mmol) in toluene (60 mL) was added. The reaction was then heated to 80 ℃, kept stirring for 5 h, and cooled down to room temperature before it was quenched by saturated NH 4 Cl solution (120 mL). After extraction with EtOAc (150 mL×3), the combined organics were washed with brine (300 mL), dried over Na 2 SO 4 , and concentrated.…”
Section: Experimental Procedures and Characterization Datamentioning
confidence: 99%
“…The reaction was then heated to 80 ℃, kept stirring for 5 h, and cooled down to room temperature before it was quenched by saturated NH 4 Cl solution (120 mL). After extraction with EtOAc (150 mL×3), the combined organics were washed with brine (300 mL), dried over Na 2 SO 4 , and concentrated. The residue was subjected to flash chromatography on silica gel eluting with PE/EtOAc (15∶1, V∶V) to afford alkene 35 (3.9 g, 72%) as a white solid.…”
Section: Experimental Procedures and Characterization Datamentioning
confidence: 99%
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