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Breaking the cis rule: L-Proline and not as expected D-proline led to (−)-amathaspiramide F with the correct configuration in a short sequence of steps (see retrosynthetic scheme). This synthesis features an exception to the principle of self-regeneration of chirality and a strategy for circumventing a problematic Nef reaction in the presence of densely spaced polar functionality.
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Hughes et al. (2002) studied this question.
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