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The synthesis of the epoxide 5 proceeds through the alkylation of 2-lithio-1,3-dithiane with (R)-epichlorohydrin (97% ee, Aldrich): a) M. Braun, D. Seebach, Chem. Ber. 1976, 109, 669; b) D. Seebach, I. Willert, A. Beck, B. T. Groebel, Helv. Chim. Acta 1978, 61, 2510.
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The bromide 10 is available from the corresponding homoallylic alcohol by tosylation (TsCl, D MAP, pyridine; 98%), followed by exchange with lithium bromide (DME 50°C; 65%). For the synthesis of the starting homoallylic alcohol, see: J. D. White, G. N. Reddy, G. O. Spessard, J. Am. Chem. Soc. 1988, 110, 1624.
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0041936119
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note
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The epoxide 11 is available from D-malic acid in four steps. (equation presented)
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27
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0042937801
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note
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A complete study of matched and mismatched elements of stereochemistry will be detailed in further reports devoted to the asymmetric-allylation process.
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0042937800
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note
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Either of the diastereomeric alcohols (R or S at C17) could potentially be a valuable intermediate toward lactone 2, depending on the strategy chosen: macrocyclization with retention of configuration at C17 (Yamaguchi protocol) or Mitsunobu macrocyclization with inversion of configuration at C17. For example, compare the reports of references [4a] and [5b].
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36
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