Synthesis of nor-sesquiterpene spirolactones and their steroidal hybrids revisited. The neopentyl dilemma: misassignment of one stereocentre may necessitate a completely new approach |
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| Institution: | 1. The Audit Department of Henan University, Kaifeng 475004, China;2. Key Lab for Special Functional Materials of Ministry of Education, Henan University, Kaifeng 475004, China;3. Quality and Technical Supervision, Inspection and Testing Center of Puyang, Puyang 457000, China;1. College of Science, Northwest A&F University, Yangling, Shaanxi Province, 712100, China;2. Department of Natural Products Chemistry, School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai, 201203, China;1. Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan;2. Diagnostic Unit for Amyloidosis, Department of Laboratory Medicine, Kumamoto University Hospital, 1-1-1 Honjo, Kumamoto 860-8556, Japan;3. Department of Neurology, Graduate School of Medical Sciences, Kumamoto University, 1-1-1 Honjo, Kumamoto 860-8556, Japan;4. Faculty of Science and Technology, Sophia University, 7-1 Kioi-Cho, Chiyoda-ku, Tokyo 102-8554, Japan;5. Department of Chemistry, Graduate School of Sciences, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan |
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| Abstract: | Inversion at the highly congested C1 position of 1-epi-pathylactone A (1-epi-1), or its corresponding steroidal hybrid 8a, using a diverse range of published procedures including microwave assisted Mitsunobu reaction or via oxidation to the corresponding ketone and subsequent reduction, was unsuccessful in our hands. Attempts to convert the C1 hydroxyl group into its corresponding chloride, en route to napalilactone 2a, also failed. Precursors with the C1α configuration installed at early stage proved not to be amenable to the targets under a broad range of conditions. |
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