DOI: 10.1246/cl.1983.385. AN ASYMMETRIC SYNTHESIS OF BICYCLIC LACTONES AND ITS APPLICATION TO THE ASYMMETRIC SYNTHESIS OF (1R,3S)-CIS-CHRYSANTHEMIC ACID

AN ASYMMETRIC SYNTHESIS OF BICYCLIC LACTONES AND ITS APPLICATION TO THE ASYMMETRIC SYNTHESIS OF (1R,3S)-CIS-CHRYSANTHEMIC ACID

10.1246/cl.1983.385

Crossref journal-article

Oxford University Press (OUP)

Chemistry Letters (286)

Abstract

Abstract Optically active bicyclic lactones are synthesized from ircides, derived from (R)-(−)-2-amino-2-phenylethanol and meso-cyclic-1,2-cis-dicarboxylic acids, by successive treatment with sodium bis(2-methoxyethoxy)aluminum hydride and sodium borohydride, followed by acid hydrolysis. This reaction is successfully applied to the asymmetric synthesis of (1R,3S)-cis-chrysanthemic acid.

Bibliography

Mukaiyama, T., Yamashita, H., & Asami, M. (1983). AN ASYMMETRIC SYNTHESIS OF BICYCLIC LACTONES AND ITS APPLICATION TO THE ASYMMETRIC SYNTHESIS OF (1R,3S)-CIS-CHRYSANTHEMIC ACID. Chemistry Letters, 12(3), 385â388.

Authors 3

Teruaki Mukaiyama (first)
Hiroyuki Yamashita (additional)
Masatoshi Asami (additional)

References 12 Referenced 33

10.1021/ja00381a024
10.1016/S0040-4039(01)82939-7
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10.1021/ja00371a073
10.1039/CT8875100240
10.1002/hlca.19280110175
10.1002/cber.188401701314
{'key': '2024011917255734200_r8'}
{'key': '2024011917255734200_r9'}
{'key': '2024011917255734200_r10'}
{'key': '2024011917255734200_r11'}
{'key': '2024011917255734200_r12'}

Dates

Type	When
Created	19 years, 1 month ago (July 24, 2006, 10:36 p.m.)
Deposited	1 year, 7 months ago (Jan. 19, 2024, 12:26 p.m.)
Indexed	1 week, 3 days ago (Aug. 23, 2025, 1:02 a.m.)
Issued	42 years, 6 months ago (March 1, 1983)
Published	42 years, 6 months ago (March 1, 1983)
Published Online	19 years, 5 months ago (March 27, 2006)
Published Print	42 years, 5 months ago (March 5, 1983)

Funders 0

None

BibTeX

@article{Mukaiyama_1983, title={AN ASYMMETRIC SYNTHESIS OF BICYCLIC LACTONES AND ITS APPLICATION TO THE ASYMMETRIC SYNTHESIS OF (1R,3S)-CIS-CHRYSANTHEMIC ACID}, volume={12}, ISSN={1348-0715}, url={http://dx.doi.org/10.1246/cl.1983.385}, DOI={10.1246/cl.1983.385}, number={3}, journal={Chemistry Letters}, publisher={Oxford University Press (OUP)}, author={Mukaiyama, Teruaki and Yamashita, Hiroyuki and Asami, Masatoshi}, year={1983}, month=mar, pages={385–388} }

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