A facile and efficient synthesis of 4-hydroxy-2,6-cis-tetrahydropyrans via tandem cross-metathesis/thermal S(N)2' reaction: protecting-group-free synthesis of (+/-)-diospongin A.
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, Journal Article
Lee, K; Kim, H; Hong, J
Published in: Organic letters
November 2009
The tandem cross-metathesis/thermal S(N)2' reaction was explored for the facile and efficient synthesis of 4-hydroxy-2,6-cis-tetrahydropyrans. The mildness of the thermal conditions allowed for the synthesis of 4-hydroxy-2,6-cis-tetrahydropyrans from base-sensitive substrates without the use of protecting groups. The tandem reaction enabled a protecting-group-free synthesis of (+/-)-diospongin A.
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Published In
Organic letters
DOI
EISSN
1523-7052
ISSN
1523-7060
Publication Date
November 2009
Volume
11
Issue
22
Start / End Page
5202 / 5205
Related Subject Headings
- Temperature
- Stereoisomerism
- Pyrans
- Organic Chemistry
- Molecular Conformation
- 34 Chemical sciences
- 03 Chemical Sciences
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Lee, K., Kim, H., & Hong, J. (2009). A facile and efficient synthesis of 4-hydroxy-2,6-cis-tetrahydropyrans via tandem cross-metathesis/thermal S(N)2' reaction: protecting-group-free synthesis of (+/-)-diospongin A. Organic Letters, 11(22), 5202–5205. https://doi.org/10.1021/ol902125d
Lee, Kiyoun, Hyoungsu Kim, and Jiyong Hong. “A facile and efficient synthesis of 4-hydroxy-2,6-cis-tetrahydropyrans via tandem cross-metathesis/thermal S(N)2' reaction: protecting-group-free synthesis of (+/-)-diospongin A.” Organic Letters 11, no. 22 (November 2009): 5202–5. https://doi.org/10.1021/ol902125d.
Lee K, Kim H, Hong J. A facile and efficient synthesis of 4-hydroxy-2,6-cis-tetrahydropyrans via tandem cross-metathesis/thermal S(N)2' reaction: protecting-group-free synthesis of (+/-)-diospongin A. Organic letters. 2009 Nov;11(22):5202–5.
Lee, Kiyoun, et al. “A facile and efficient synthesis of 4-hydroxy-2,6-cis-tetrahydropyrans via tandem cross-metathesis/thermal S(N)2' reaction: protecting-group-free synthesis of (+/-)-diospongin A.” Organic Letters, vol. 11, no. 22, Nov. 2009, pp. 5202–05. Epmc, doi:10.1021/ol902125d.
Lee K, Kim H, Hong J. A facile and efficient synthesis of 4-hydroxy-2,6-cis-tetrahydropyrans via tandem cross-metathesis/thermal S(N)2' reaction: protecting-group-free synthesis of (+/-)-diospongin A. Organic letters. 2009 Nov;11(22):5202–5205.
Published In
Organic letters
DOI
EISSN
1523-7052
ISSN
1523-7060
Publication Date
November 2009
Volume
11
Issue
22
Start / End Page
5202 / 5205
Related Subject Headings
- Temperature
- Stereoisomerism
- Pyrans
- Organic Chemistry
- Molecular Conformation
- 34 Chemical sciences
- 03 Chemical Sciences