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【结 构 式】 
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【分子编号】52833 【品名】(5S)-2,2,7-trimethyl-1,3-dioxaspiro[4.4]non-6-ene 【CA登记号】 |
【 分 子 式 】C10H16O2 【 分 子 量 】168.23584 【元素组成】C 71.39% H 9.59% O 19.02% |
合成路线1
该中间体在本合成路线中的序号：(V)The chiral cyclohexenone intermediate (VII) was prepared as follows. Epoxide ring opening of (S)-glycidol (I) with the Grignard reagent (II) produced diol (III), which was protected as the isopropylidene ketal (IV) by treatment with 2,2-dimethoxypropane. Addition of bromine to olefin (IV) and further cyclization of the resultant dibromide in the presence of potassium hexamethyldisilazide gave rise to the spiro cyclopentene (V). Ozonolysis of (V), followed by reductive work-up, yielded the keto aldehyde (VI), which upon treatment with KOH underwent intramolecular aldol condensation to the target cyclopentenone (VII).
| 【1】 Taber, D.F.; et al.; Synthesis of (-)-fumagillin. J Am Chem Soc 1999, 121, 23, 5589. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 19241 | (2S)oxiranylmethanol | 60456-23-7 | C3H6O2 | 详情 | 详情 |
| (II) | 52830 | 2-Methylallylmagnesium chloride | C4H7ClMg | 详情 | 详情 | |
| (III) | 52831 | (2R)-5-methyl-5-hexene-1,2-diol | C7H14O2 | 详情 | 详情 | |
| (IV) | 52832 | (4R)-2,2-dimethyl-4-(3-methyl-3-butenyl)-1,3-dioxolane | C10H18O2 | 详情 | 详情 | |
| (V) | 52833 | (5S)-2,2,7-trimethyl-1,3-dioxaspiro[4.4]non-6-ene | C10H16O2 | 详情 | 详情 | |
| (VI) | 52834 | (4R)-2,2-dimethyl-4-(3-oxobutyl)-1,3-dioxolane-4-carbaldehyde | C10H16O4 | 详情 | 详情 | |
| (VII) | 52835 | (5S)-2,2-dimethyl-1,3-dioxaspiro[4.5]dec-6-en-8-one | C10H14O3 | 详情 | 详情 |