Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 2, Pages 593-605Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo052001l
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- NIGMS NIH HHS [GM30938] Funding Source: Medline
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Two model studies in support of a total synthesis of the complex polycyclic alkaloid daphnilactone B have been completed. The objectives of the models studies were to demonstrate the use of a tandem double-intramolecular [4+2]/[3+2] nitroalkene cycloaddition for the stereocontrolled construction Of four of the rings in the core of the natural product. The first model Study established the ability to create a pyrrolidine ring corresponding to ring A of daphnilactone B through a modification of the dipolarophile and Subsequent functional group manipulations. The second model study required the modification of the dienophile in the [4+2] cycloaddition to accommodate the formation of a piperidine ring (ring B of daphnilactone 13). Nitroalkene 26 containing a diene as the dienophile served well in the tandem cycloaddition to afford the nitroso acetal 38a in 77% yield. Subsequent functional group manipulations allowed for the high-yielding conversion to the core of daphnilactone B.
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