21,22-Dihydro-isocytochalasin A | 59861-42-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: 21,22-Dihydro-isocytochalasin A
• 英文别名: (16S)-7β,9-dihydroxy-16-methyl-1,20-dioxo-10-phenyl-9,23-seco-[13]cytochalasa-6(12),13t-dien-23-oic acid 7-lactone
• CAS: 59861-42-6
• 化学式: C₂₉H₃₇NO₅
• 分子量: 479.616
• InChiKey: GJRXYJZXCZQBMI-QWWWBKLZSA-N

反应信息

• 作为产物：
  描述：

  β-Cytochalasinsaeure 在 2,2'-二硫二吡啶 、 三苯基膦 作用下， 以 xylene 为溶剂， 生成 21,22-Dihydro-isocytochalasin A
  参考文献：
  名称：

  Cytochalasin B (Phomin): Abbaureaktionen und Cyclisierung der B-Cytochalasinsäure zu 21,22-Dihydro-isocytochalasin A

  摘要：

  Cytochalasin B (Phomin): Degradation Reactions and Cyclization of B‐Cytochalasinic Acid to 21,22‐Dihydro‐Isocytochalasin ATreatment of the γ‐lacton 5, a transformation product of cytochalasin B (phomin) (1), with OsO4 gave the dihydroxy derivatives 6 and 7. Cleavage of the former by NaIO4 in aqueous methanol yielded a mixture of the dimethylacetal 10 and the unsaturated aldehyde 11, which are potential intermediates for a total synthesis of cytochalasins. Cytochalasin B (1) was hydrolysed with NaOH in aqueous dioxane to B‐cytochalasinic acid (14). Recyclization of 14 using the Mukaiyama‐Corey method [19] [20] did not yield cytochalasin B (1) but the isomeric 21,22‐dihydro‐isocytochalasin A (18). Treatment of 14 according to Gerlach [21] yielded the phthalimidine 19.

  DOI：

  10.1002/hlca.19760590322