Zur Konstitution des „Tetracyclosqualens”︁

Sandermann, Wilhelm; Casten, Reinhard

doi:10.1002/lipi.19650671108

Cited by 2 publications

(1 citation statement)

References 13 publications

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“…The last two projected target molecules of our series were the spiro[4.6]undecanone 30 and the spiro[4.7]dodecanone 31 (Figure 4). A cyclooctane ring is very well able to mimic the steric bulk of a dimethylcyclohexane ring, as we had observed in the synthesis of violet odorants, 30 and as was also reported for theaspirane analog by Weyerstahl et al 31 and for Ambrox ® derivatives by Sandermann et al 32 Thus, especially 31 seemed to be an interesting synthetic target, and with 2.5 ng/L air it indeed possessed a threshold similar to 11 while also being close in odor to this lead. Even the spiro[4.6]undecanone 30 possessed a pronounced vetiver character with a moderate threshold of 9.4 ng/L air.…”

Section: Methodssupporting

confidence: 79%

Design, Synthesis and Structure-Odor Correlation of Novel Spiro[4.5]-decan-2-ones

Kraft¹,

Cadalbert²

2002

Synthesis

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Dehydration and Rupe rearrangement of 2-(3,3-dimethylcyclohexyl)hex-3-yne-2,5-diol (9) furnished as a 3% byproduct the intense vetiver-like smelling 4,7,7-trimethyl-1-methylenespiro[4.5]decan-2-one (11). Motivated by the commercial importance of vetiver oil and the lack of synthetic substitutes as well as the lack of insight into the structural requirements for vetiver odorants, an efficient synthetic route to vetiver-like smelling compounds was developed. It consists of Wittig-Horner-Emmons reaction of diverse cycloalkanones with triethyl 2-phosphonopropionate, subsequent Grignard reaction with in situ conversion to the trienolate, and classical Nazarov cyclization of the resulting dienones. This route not only leads to 11 in 61% yield in the final Nazarov cyclization, but also to 16 analogs, which provide insight into both, the Nazarov reaction and the structure-odor relationship of vetiver odorants. Other vetiver-like smelling compounds discovered include (1RS,4SR,5SR)-1,4,7,7-tetramethylspiro[4.5]decan-2-one (16), 4-methyl-1-methylenespiro[4.6]undecan-2-one (30) and 4-methyl-1-methylenespiro[4.7]dodecan-2-one (31).

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Section: Methodssupporting

confidence: 79%