New synthetic routes to spiroacetals. The 3,4-dihydro-2H-pyran approach to (±)-talaromycin B

Abstract
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.

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