Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 124, Issue 33, Pages 9812-9824Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja0204675
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Funding
- NCI NIH HHS [CA08748, T32-CA62948] Funding Source: Medline
- NHLBI NIH HHS [HL25848] Funding Source: Medline
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The total synthesis of (+/-)-gelsemine (1) is described. A defining phase of the effort involved recourse to a strategic oxetane ring (see compound 25). It was constructed anticipating an intramolecular displacement of the carbon (C17)-oxygen (O4) bond (see product 48). A key intermediate in the stereospecific elaboration of the oxetane linkage was enone 22, which was susceptible to two beta-face attacks leading to 24 and, thence, 25. Three sigmatropic rearrangements were employed in building the bridgehead (C20) and the spiroanilide (C7) quaternary centers en route to gelsemine.
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