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A formal total synthesis of erythromycin A. 2. A convergent synthesis of Woodward's carbamate intermediate

✍ Scribed by Tadashi Nakata; Mineo Fukui; Takeshi Oishi

Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 264 KB
Volume: 29
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)86717-9

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✦ Synopsis

In the preceding paper. the syntheses of the optically active two segments (+)-2 and (-)-2 having most of chiral centers involved in erythronolide A were reported.

In this report, coupling reaction of these two segments and the subsequent elaboration leading to carbamate 1.

a key intermediate in Woodward's erythromycin A synthesis. are described.

Aldol strategy is quite promising for this purpose since the reaction between Z-enolate of 2 and aldehyde 2 is presumed to proceed through the transition state 1 (Fig.

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