Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 72, Issue 13, Pages 4596-4610Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo062422i
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- NIGMS NIH HHS [GM-29028] Funding Source: Medline
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A first-generation strategy for construction of (+)-nodulisporic acids A (1) and B (2) is described. The strategy entails union of the eastern and western hemisphere subtargets via the indole synthesis protocol developed in our laboratory. Subsequent elaboration of rings E and F, however, revealed the considerable acid instability of the C(24) hydroxyl, thereby preventing further advancement. Nonetheless, preparation of the heptacyclic core of (+)-nodulisporic acids A and B, the total synthesis of (+)-nodulisporic acid F, the simplest member of the nodulisporic acid family, and elaboration of the heptacyclic core of (-)-nodulisporic acid D were achieved.
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