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Formal total synthesis of (−)-anisomycin based on the stereoselective nucleophilic substitution along with aryl migration

✍ Scribed by Machiko Ono; Keiko Suzuki; Hiroyuki Akita

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 306 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)01715-3

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✦ Synopsis

The stereoselective conversion of (4R)-5-hydroxy-4-(4'-methoxyphenyl)-2(E)-pentenoate 5 into the (4S)-4hydroxy-S-(4'-methoxyphenyl)-2(E)-pentenoate 6 using an AgNOs/MS 4&MeNOz system was accomplished along with complete inversion at the CJ-position, and the synthesis of the intermediate (4S)-7 for the chiral synthesis of (-)-anisomycin 8 from (4S)-6 based on osmium tetroxide-catalyzed stereoselective dihydroxylation was achieved.

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