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Synthetic study of aquayamycin. Part 3: First total synthesis

โœ Scribed by Takashi Matsumoto; Hiroki Yamaguchi; Mitsujiro Tanabe; Yoshizumi Yasui; Keisuke Suzuki

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
76 KB
Volume
41
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

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 framework.

๐Ÿ“œ SIMILAR VOLUMES

Synthetic study of aquayamycin. Part 2:
Synthetic study of aquayamycin. Part 2: Synthesis of the AB ring fragment
โœ Hiroki Yamaguchi; Tadayoshi Konegawa; Mitsujiro Tanabe; Takeshi Nakamura; Takash ๐Ÿ“‚ Article ๐Ÿ“… 2000 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 64 KB

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.

Synthetic study of aquayamycin. Part 1:
Synthetic study of aquayamycin. Part 1: Synthesis of 3-(phenylsulfonyl)phthalides possessing a ฮฒ-C-olivoside
โœ Takashi Matsumoto; Hiroki Yamaguchi; Toshiyuki Hamura; Mitsujiro Tanabe; Yokusu ๐Ÿ“‚ Article ๐Ÿ“… 2000 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 84 KB

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.