Synthetic study of aquayamycin. Part 2: Synthesis of the AB ring fragment
โ Scribed by Hiroki Yamaguchi; Tadayoshi Konegawa; Mitsujiro Tanabe; Takeshi Nakamura; Takashi Matsumoto; Keisuke Suzuki
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 64 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
A highly oxygen-functionalized cyclohexenone 2, the AB ring fragment for the aquayamycin synthesis, was efficiently synthesized via stereoselective addition of allylzinc bromide to ketone 3a which, in turn, was available from the optically pure cyclohexane 1,2,3-triol derivative 5.
๐ SIMILAR VOLUMES
The first total synthesis of aquayamycin (1) has been accomplished. The crucial steps include (1) the Hauser reaction between 3-(phenylsulfonyl)phthalide 3 and cyclohexenone 4 to make up the linear BCD tricycle, and (2) the intramolecular pinacol coupling of keto aldehyde 7 to the full tetracyclic f
An efficient synthetic route to 3-(phenylsulfonyl)phthalides possessing a b-C-olivoside was developed by exploiting the regioselective [2+2] cycloaddition of benzyne with ketene silyl acetal. The compounds are useful in the total synthesis of the angucyclines, including aquayamycin.