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Stereoselective one-pot three-component coupling approach towards the synthesis of the AC ring system of taxanes

✍ Scribed by Takayuki Serizawa; Shigeru Miyamoto; Yoshitaka Numajiri; Shinichiro Fuse; Takayuki Doi; Takashi Takahashi

Book ID
104096345
Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
284 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

The stereoselective one-pot three-component coupling reaction was accomplished by 1,4-addition of the protected cyanohydrin ether 9f to cyclohexenone 10g and subsequent addition of the resulting enolate to formaldehyde in high yield for the formation of the AC ring system of taxanes. We found that the bulky substituents at the 10-position in the A ring prevent the desired 1,4-addition. Similarly, the bulky trialkylsiloxy groups at the 4-position in the C ring prevent the 1,4-addition and electron-donating alkoxy groups at the same position induce the undesired retro-Michael reaction.

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