1983 Fiscal Year Final Research Report Summary
Studies on the synthesis of biologically active alkaloids employing chiral oxazoline blocks
| Project/Area Number |
59550597
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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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| Research Field |
Synthetic chemistry
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| Research Institution | Okayama University |
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Principal Investigator |
MORIWAKE Toshio Okayama University, Department of Applied Chemistry, Professor, 工学部, 教授 (30032923)
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| Co-Investigator(Kenkyū-buntansha) |
INABA Masami Okayama University, Department of Applied Chemistry, Instructor, 工学部, 助手 (00033241)
SAITO Seiki Okayama University, Department of Applied Chemistry, Associate Professor, 工学部, 助教授 (60033239)
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| Project Period (FY) |
1984 – 1985
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| Keywords | Chiral Oxazoline / Amino Acids / Biologically Active Alkaloids / Cyclic Imidates / Amide Synthesis / Chiral Allyl Amines / gamma-Amino Allylic Alcohols / Amino Chiral Synthons |
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| Research Abstract |
This research aims at developing useful chiral synthons (amino chiral synthons) which should enjoy large popularity in synthesizing various bioactive alkaloids. What is required for these amino chiral synthons is the installation of definite stereocenters adjacent to nitrogen atoms involved in such biologically active substances. We have considered that a possible starting material matching to this requisite is optically active alpha-amino acids and have been intrigued with the development of otherwise inaccessible amino chiral synthons through their functional-group transformation. In this context we must recognize that if we want to keep their stereochemical integrity and amino groups intact throughout the course of the transformation, the most important points is how we can elaborate novel amino chiral synthons from amino alcohols or amino aldehydes derivable via appropriate reduction of alpha-amino acids. Accordingly we have fixed our attention to(1)the conversion of the amino alco
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hols to cyclic imidates, their transformation to imidatonium ions, and submission of the imidatonium ions to novel nucleophilic ring opening processes, and(2)synthesis of chiral allyl amines or 4-aminoallylic alcohols from the amino aldehydes without racemization. Our efforts toward these ends have been rewarded with some fruitful results. With regard to the objective(1), we have succeeded in establishing a novel non-condensative method for synthesizing amides by nucleophilic ring opening of the imidates relying on reasonable choice of nucleophiles. With regard to(2) , non-basic organometallic reagent developed by Nozaki-Ohshima gave a solution to give various allyl amines from the amino aldehydes without racemization and, in addition, we have found the reaction conditions under which 4-amino-alpha, beta-unsaturated esters can be reduced in a 1,2-fashion to give chiral 4-aminoallylic alcohols. Thus-obtained amino chiral synthons have been successfully employed for the syntheses of natural alkaloids and some nitrogen compounds of biological interests. Less
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Research Products
(24 results)
