Add time:09/27/2019         Source:sciencedirect.com

The acylation of the (±)-spiro-γ-lactone 1 lithium enolate (3 equiv) by the O-TBDMS methyl (−)-(S)-lactate, the O-TBDMS methyl (+)-(S)-mandelate, or the diacetone-d-glucose carbonate (1 equiv each) occurs with a kinetic resolution. The (S,S)-enolate is the most reactive with the lactate and it is the (R,R)-enolate, which selectively reacts with the mandelate or the DAG carbonate. After alkylation of the resulting acyl lactones with 4- or 5-methoxy-1-iodobenzocyclobutene and heating, title compounds were obtained and, after deprotection, the structures of the optically pure new steroids were ascertained by single crystal X-ray analysis.

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