Four out of the five rings of the alkaloid neotuberostemonine (1) are present in the advanced precursor 2. The tetracyclic compound 2 has now been prepared in a short, linear route via lactone acid 3. A key step in the synthesis was the cuprate-mediated SN2′ ring-opening desymmetrization of the C2-symmetric bislactone 4.
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Booker‐Milburn et al. (2003) studied this question.
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