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Short Syntheses of (±)-Grandisol and (±) Lineatin via, a common Intermediate (1987)

Aljancic-Solaja, Ivana ; Rey, Max ; Dreiding, André S.

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 70 (1987), S. 1302-1306

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: A 6-step synthesis of (±)-grandisol (1) is presented, which involves dichloroketene addition to 3-methyl-3-butenyl acetate (4), reductive dechlorination of the adduct 6 to the ketone 7 and saponification to 8, aldolization of 7 or 8 with acetone and cyclization to the bicyclic ketone 9, Wolff-kishner, reduction to 14, and finally ring opening to 1. Since 9 is a known intermediate of the synthesis of (±)-lineatin (2), the latter can now be obtained in 6 steps.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19870700510

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