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A Concise Synthesis of (E)- and (Z)-Neomanoalides (1994)

Jefford, Charles W. ; Rossier, Jean-Claude ; Boukouvalas, John ; [et al.]

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 77 (1994), S. 661-667

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The first synthesis of (Z)-neomanoalide (4) and an improved synthesis of its (E)-isomer 3 was accomplished in a concise, regiocontrolled manner by exploiting 2-[(tert-butyl)dimethylsiloxy]-4{[(tert-butyl)dimethylsiloxy]-methyl}furan (6) as the key reagent. Lithiation of 6 and subsequent reaction with the (2Z)- or (2E)-isomer of (6E)-3-{[(tert-butyl)dimethylsiloxy]methyl}-7-methyl-9-(2′,6′,6′-trimethylcyclohex-1′-enyl)nona-2,6-dienyl bromide (5), followed by hydrolysis, afforded the corresponding neomanoalide.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19940770309

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