The nucleophilic cleavage of the oxirane (9) by the organocuprate derived from 3-ethyl-6-lithio-3,4-dihydro-2H-pyran (7) was the key step in a synthesis of racemic talaromycin B (12). A similar synthesis of desethyltalaromycin B (15) from (9) and 6-lithio-3,4-dihydro-2H-pyran was achieved.
P. Kocienski and C. Yeates, J. Chem. Soc., Perkin Trans. 1, 1985, 1879 DOI: 10.1039/P19850001879
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