16049-28-8Relevant articles and documents
Hydrolysis and Selective Reduction with Yeast: Enantiospecific Synthesis of Antirhine from Secologanin
Brown, Richard T.,Dauda, Bukar E. N.,Santos, Cid A. M.
, p. 825 - 826 (1991)
Glucoside hydrolysis and chemoselective reduction of secologanin ethylene acetal 2 with baker's yest affords a C-1 reduced aglucone 4 from which (+)-antirhine 8 is obtained in a four-step sequence.
A total synthesis of (-)-antirhine
Suzuki,Sato,Unno,Kametani
, p. 3135 - 3141 (1986)
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Biomimetic synthesis of monoterpenoid indole alkaloids from aglucones of secologanin derivatives: pH controlled product selectivity
Brown
, p. 609 - 616 (2007/10/03)
Variation of the pH for hydrolysis of secologanin derivatives with β-glucosidase controls rearrangement of the aglucone to afford different products, and hence stercoselective syntheses of heteroyohimbine, yohimbine and Aspidosperma-type alkaloids; with baker's yeast chemoselective reduction can also be achieved to give a precursor for antirhine and related alkaloids.
A Highly Enantioselective Synthesis of (-)-Antirhine by Chemo-Enzymatic Approach
Danieli, Bruno,Lesma, Giordano,Mauro, Marina,Palmisano, Giovanni,Passarella, Daniele
, p. 8837 - 8852 (2007/10/02)
(-)-Antirhine 2 was synthesized in an efficient and stereocontrolled fashion from the readily available (1R-2S)-cyclohexene dimethanol monoacetate 6.A key step was the regio- and stereoselective Pictet Spengler cyclization of the masked dialdehyde 12 to t
