期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 72, 期 25, 页码 9736-9745出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo701821h
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资金
- NIGMS NIH HHS [R01 GM063755-09, GM-063755, R01 GM063755] Funding Source: Medline
[GRAPHICS] Synthetic studies toward the total synthesis of (+)-acutiphycin (1) resulted in the discovery of additive-free, highly regioselective nickel -catalyzed reductive coupling reactions of aldehydes and 1,6-enynes and the construction of an advanced intermediate in studies directed toward the synthesis of 1. Ultimately, although not employing the nickel-catalyzed reaction, a highly convergent total synthesis of (+)-acutiphycin featuring an intermolecular SMI2-mediated Reformatsky coupling reaction and macrolactonization initiated by a retro-ene reaction of an alkoxyalkyne was achieved. The resulting synthesis was 18 steps in the longest linear sequence from either methyl acetoacetate or isobutyraldehyde.
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