Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 3, Pages 1205-1211Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo802387c
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Funding
- Ministry of Science and Technology (Spain)-FEDER [CTQ2006-02390/BQU]
- DURSI
- Generalitat de Catalunya [2005SGR-0603]
- Fundacao para a Ciencia a Tecnologia
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The enantioselective construction of the 3-ethylindolo[2,3-a]quinolizidine moiety present in numerous indole alkaloids is reported, the key steps being a stereoselective cyclocondensation of (S)-tryptophanol with an appropriate racemic delta-oxoester and a regio- and stereoselective cyclization of the resulting oxazolopiperidones on the lactam carbonyl group. A new procedure for the removal of the hydroxymethyl auxiliary group, involving oxidation to an aldehyde, dehydration of the corresponding oxime, and reductive decyanation of the resulting alpha-aminonitrile, has been developed. The preparation of indoloquinolizidine 27 represents a formal total synthesis of (+)-dihydrocorynantheine, (-)-dihydrocorynantheol, and other indolo[2,3-a]quinolizidine and oxindole alkaloids bearing the same substitution pattern.
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