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ChemInform Abstract: Synthesis of rac-(E)-Opposita-4(15),7(11)-dien-12-al.

โœ Scribed by Peter Weyerstahl; Helga Marschall; Peter Degenkolb; Philippine Lebada


Publisher
John Wiley and Sons
Year
2010
Weight
32 KB
Volume
30
Category
Article
ISSN
0931-7597

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โœฆ Synopsis


Synthesis of rac-(E)-Opposita-4(15),7(11)-dien-12-al.

-The title sesquiterpene aldehyde (XIII) is prepared starting from commercially available methylcyclohexenone (I) via a diastereoselective tandem alkylation of compound (I), a chemoselective hydroboration of vinyl group in compound (V) and a Wittig-Horner olefination to introduce the formylpropenyl side chain into aldehyde (X). Compound (XIII) is shown to be an olfactorily important con-


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Synthesis of rac-(E)-Opposita-4(15),7(11
โœ Peter Weyerstahl; Helga Marschall; Peter Degenkolb; Philippine Lebada ๐Ÿ“‚ Article ๐Ÿ“… 1999 ๐Ÿ› John Wiley and Sons ๐ŸŒ English โš– 219 KB

E)-Opposita-4(15),7(11)-dien-12-al / Natural products / Vetiver oil / Octahydroindene derivatives / Fragrances rac-(E)-Opposita-4(15),7(11)-dien-12-al (1) was synthesized Vetiver oil. Synthetic rac-1 has a strong, green woody odor with soft-floral undertones, which confirms that 1 is an in 12 steps

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The synthesis of "09R#!"E#!acora!2\6"00#!dien!01!al "0# is described starting from the enanti! omerically pure "ยฆ#!pulegenic acid "3# via the Diels!Alder adducts 7a\b[ The odour of the new sesquiterpene aldehyde was typically aldehydic\ fruity and leathery[