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note
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We are indebted to Dr. G. Fráter of Givaudan Dübendorf AG for a gift of racemic Georgywood.
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note
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Although synthetic 1 was contaminated by about 10% of the (1S,2S)-diastereomer, there is no contribution of this impurity to odor since it is essentially odorless, as shown in a later section of this paper.
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note
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Odor testing was carried out with several members of our research group, including the authors, with good agreement on the consensus evaluation of odor.
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note
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The Diels-Alder reaction can be carried out using an excess of the racemic diene 17 because of a faster rate of reaction for the (R)- vs the (S)-enantiomer, an interesting illustration of the efficacy of catalyst 5. This is an unusual example of kinetic resolution in a catalytic enantioselective Diels-Alder reaction.
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37
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note
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The results that are summarized in Scheme 7 also show that this particular Diels-Alder reaction is not useful for the synthesis of (+)-2, although we entertained this possibility when considering alternative synthetic routes to 2 that are simpler than the one set out in Scheme 2.
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40
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note
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For details of X-ray diffraction analysis of the tosylhydrazone of 38, see the Supporting Information.
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