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Synthesis of the C(1)–C(8) segment of (+)-acutiphycin

✍ Scribed by Joey-Lee Methot; Louis Morency; Philip D. Ramsden; Jerome Wong; Serge Léger

Book ID
104232423
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
107 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

The synthesis of the pyran segment of (+)-acutiphycin was achieved using an intramolecular Lewis acid-catalyzed reaction between a silyl enol ether and an ortho ester.

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The CI-C9 segment of epothilons was generated by an aldol reaction between chiral aldehyde 3 and ethyl ketone 4. Removal of the TBS protecting groups and debenzylation generated spiro ketal 13 which was analyzed by X-ray crystallography.