| Project/Area Number |
12672082
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | RIKEN (The Institute of Physical and Chemical Reseach) |
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Principal Investigator |
SHIMIZU Takeshi RIKEN(The Institute of Physical and Chemical Reseach), Synthetic Organic Chemistry Laboratory, Senior Scientist, 有機合成化学研究室, 副主任研究員 (80087569)
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| Project Period (FY) |
2000 – 2001
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| Project Status |
Completed (Fiscal Year 2001)
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| Budget Amount *help |
¥3,400,000 (Direct Cost: ¥3,400,000)
Fiscal Year 2001: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2000: ¥2,500,000 (Direct Cost: ¥2,500,000)
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| Keywords | reveromycin A / inhibitor of eukaryotic cell growth / inhibitor of protein synthesis / anti-tumor agent / 6, 6-spiroacetal / asymmetric total synthesis / succinylation / reaction under high pressure / 6,6-スピロケタール / Julia olefination |
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| Research Abstract |
Reveromybin A is a novel polyketide-type antibiotic produced by Steptomyces sp. and inhibits mitogenic activity induced by the epidennal growth factor in a mouse epidermal keratinocyte. The characteristic structural features of reveromycin A include a 1, 7-dioxaspiro[5.5]undecane moiety, that is, the 6, 6-splroacetal system bearing a hemisuccinate, two alkenyl carboxylic acids, and methyl and n.-butyl groups. The first total synthesis of reveromycin A has been designed and accomplished. Our synthesis is based on the stereoselective and convergent synthesis of the 6, 6-spiroacetal system followed by the succinylation of tertiary alcohol under high pressure and the installation of the polyene-containing side chains. We also studied the syntheses and activities of reveromycin A derivatives.
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