117179-02-9Relevant articles and documents
Enantioselective formal synthesis of (-)-podophyllotoxin from (2 S,3 R)-3-arylaziridine-2-carboxylate
Takahashi, Masato,Suzuki, Noriyuki,Ishikawa, Tsutomu
, p. 3250 - 3261 (2013/06/26)
Meyers' 4-aryl-1-tetralone-lactone and ent-Zhang's 2-diarylmethyl-4- oxobutanoate were synthesized in the formal synthesis of (-)-podophyllotoxin from (2S,3R)-3-arylaziridine-2-carboxylate, via 3,3-diarylpropanoate as a common intermediate, in an overall 42% yield through 10 steps and 31% yield through 6 steps, respectively. The key steps in the synthesis were regio- and diastereoselective ring opening with an aromatic nucleophile, samarium iodide promoted reductive C-N bond cleavage, and Stille coupling for introducing the vinyl functionality. The starting aziridine was enantioselectively prepared from 3,4,5-trimethoxybenzaldehyde by guanidinium ylide mediated asymmetric aziridination. All nitrogen components used in the reaction sequence are reusable as the starting guanidinium source.
Total Synthesis of ( +/-)-Picropodophillone
Murphy, William S.,Wattanasin, Sompong
, p. 271 - 276 (2007/10/02)
Following model studies, the synthesis of (+/-)-picropodophillone was completed by first cyclopropanating the appropriate chalcone (11) with ethoxycarbonyl dimethylsulphonium methylide.Treatment of the resulting cyclopropyl ketone with stannic chloride in
