Synthesis of (+)-sch 642305 by a biomimetic transannular Michael reaction |
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Authors: | Snider Barry B Zhou Jingye |
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Affiliation: | Department of Chemistry, MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA. |
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Abstract: | [reaction: see text] The synthesis of (+)-Sch 642305 (1) has been completed in 17 steps in 1.6% overall yield. Transannular Michael reaction of 2b with NaH in THF provided cyclohexenone 23 stereospecifically. Heating 23 in TFA/CDCl(3) provided a 3:1 equilibrium mixture of 23 and 25, which was hydrolyzed to give (+)-6-epi-Sch 642305 (24) and (+)-Sch 642305 (1), respectively. |
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