期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 73, 期 24, 页码 9657-9667出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo801794s
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资金
- National Institutes of Health [GM026782]
- Ministerio de Educacion y Ciencia, Spain
A convergent and highly stereocontrolled total synthesis of the cytotoxic macrolide (+)-superstolide A is described. Key features of this synthesis include the use of bimetallic linchpin 36b for uniting the C(1)-C(15) (43) and the C(20)-C(27) (38) fragments of the natural product, a late-stage Suzuki macrocyclization of 49, and a highly diastereoselective transannular Diels-Alder reaction of macrocyclic octaene 4. In contrast, the intramolecular Diels-Alder reaction of pentaenal 5 provided the desired cycloadduct with lower stereoselectivity (6: 1: 1).
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