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Please login to access the full content or check if you have access via20.6.1.4.1 Variation 1: The Corey–Nicolaou Method
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Maier, M. E., Science of Synthesis, (2007) 20, 1456.
The Corey–Nicolaou method is based on the use of pyridine-2-thiol esters 125 that are formed in situ from the ω-hydroxy acids 123.[146] Protonation of the basic nitrogen by the hydroxy group activates the thioester and positions the nucleophilic oxygen in close proximity to the carboxy group. The tetrahedral intermediate 126 subsequently collapses to the desired lactone 127 and pyridine-2-thione (Scheme 53). The intermediate pyridine-2-thiol esters can be obtained from the ω-hydroxy esters, 2,2′-dipyridyl disulfide (124), using triphenylphosphine in xylene.
Meeeee 88 Meeeeeeee ee Meeeeeeeeeee Meeeeeeee eee Meeeeeee-8-eeeee Meeeee[888]
Meeeeeee, eeeeeeeeeeeee ee eeeeeeee ee eeeeeeeee eee eeeeeeee ω-eeeeeeeeeeeeeee-8-eeeee eeeeee eeeee eeee eeeeeeee. Mee eee eeeeee eeeeeee eeeee, eee eeeeeee eeeee ee eeeeeeee eee eeee eeee 88 (Meeee 8).[888]
Meeee 8 Meeeeeeeeeeee eeee Meeeeeee-8-eeeee Meeeee ee ω-Meeeeee Meeee[888]
| Meee Meee ee Meeeeee | Meeee ee Meeeeee (%) | Meeee ee Meeeeee (%) | Mee |
|---|---|---|---|
| 8 | 88 | 8 | [888] |
| 8 | 8 | 88 | [888] |
| 88 | 88 | 88 | [888] |
| 88 | 88 | 8 | [888] |
| 88 | 88 | 8 | [888] |
| 88 | 88 | 8 | [888] |
Meeeeeeeeeeee ee eee eeeeeeee eeeeee eeeeeee eee eee ee eeeee eeeeeeeeeeee eeeeeeeeee. Meeee eeeee, eeeeeeeee 888 eeeee ee ee eee eeee eeeeeeeee (Meeeee 88). Meeeeeeeeeee eeee eeeee eeeeeeeeee eeeeeee eeeee eeeeeeeeeeee (88°M, eeeeeeeee eeeeeee) eee eee eeeeee eee eee eeeeeeeeeeeee eeee ee ee eeeeee.[888] Meee, eeeee 888 eee eeeeeeeeeeee eeeeee eee 88-, 88-, eee 88-eeeeeeee eeeee eee 88, 88, eee 88%, eeeeeeeeeeee. Mee eeeeeeee eeeee ee eeeeeeeeeeeeeeeeee eeee eee eeeee eeeeeeeeee 888, 888, eee 888 eeee eeeee ee ee 888:88:8.
Meeeee 88 Meeee Meeeeeeeeeee Meeeeeeeee eeee eee Meee Meeeeeeee ee Meeeeeeeeeeeeeeeee[888]
Me eee Meeeeee–Meeeeeee eeeeeeeeeeee, eeeeee eeee eee eeeee ee eeeee ee eeeeeeee eee 8-eeeeeee eeeeeeeeee eee eeeeeeeeeeee ee eee eeeeee eeeeee ee eee eeeeeeee eeeeeeee.[888] Me eeee eee, eeeeeeeeeee eee eeee eeeee ee eeee eeeeeeeeeee ee eeeeeee eeeeeeee.
Mee eeee eeeeeeee, ee eeeeeeeeee eeeee- ee eeee-eeeeeeee eeee, eee eeeeeeee ee e eee eeeeee eeee ee eee eeee eeee eeeeeeeeeee eee eeeeeeeeeeeee.[888] Meeee 8 eeeeeee eeeeeeeeeeeeee eeeeeeeeeeeeee eeeee eee Meeee–Meeeeeee eeeeee.[888,888–888]
Meeee 8 Meeeeeeeeeeeee Meeeeeee eeee eee Meeeee ee eee Meeee–Meeeeeee Meeeee[888,888–888]
| Meeeeee | Meee ee Meee | Meeeeeeeee | Meeee (%) | Mee |
|---|---|---|---|---|
 |
eeeeeeeeeee | eeeeeeeee 888, eeeeeee, eeeeee | 88 | [888] |
| |
eeeeeeeeeeeee eeeeeeeee | eeeeeeeee 888, eeeeeee, 888°M, 88 e | 88 | [888] |
| |
eeeee-eeeee eeeeee | eeeeeeeee 888, MMM, 88°M, 88 e | 88 | [888] |
| |
eeeee-eeeeeeee | eeeeeeeee 888, MeMeM8 (8.88 eeeee), eeeeeee, 888°M, 88 e | 88–88 | [888] |
| |
eeee-eeeeeeee | eeeeeeeee 888, MeMeM8 (8.88 eeeee), eeeeeee, 888°M, 88 e | 88–88 | [888] |
| |
eeeeeeeee eeeeeeeee | eeeeeeeee 888, eeeeee, eeeeee, 88 e | 88 | [888] |
| |
eeeee-eeeeeeee | eeeeeeeee 888, MeMM8, eeeeeee, 888°M, 88 e | 88 | [888] |
| |
eee-eeeeeeee | eeeeeeeee 888, MeMeM8, eeeeeee, 888°M, 88 e | 88 | [888] |
References
| [146] | Meeee, M. M.; Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [147] | Meeee, M. M.; Meeeeeee, M. M., Meeeeeeeeee Meee., (8888), 8888. |
| [148] | Meeeeee, M.; Meeeeeee, M., Meee. Meee. Meee, (8888) 88, 8888. |
| [149] | Meeeee, M. M.; Meee, M.; Meeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [150] | Meeeeeeee, M.; Meee, M.; Meeeee, M.; Meeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [151] | Meeee, M. M.; Me, M.; Mee, M. M.; Meee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [152] | Meeeeeee, M. M.; MeMeeee, M. M.; Meeeee, M. M.; Mee, M. M.; Meeeeee, M. M.; Meeeeeeeeeee, M.; Meeeee, M. M. M.; Meeee, M. M.; Meee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [153] | Meeee, M. M.; Meeeeeeeee, M. M.; Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [154] | Meeeee, M. M.; Meeee, M.; Meee, M.; Meeee, M. M.; Meeee, M. M.; Meeee, M., Meeee. Meeeee., (8888) 88, 8888. |
| [155] | Meeeee, M. M.; Meee, M.-M., M. Mee. Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) M 8-8, 888.
- 8.Meeeee-Meee, (8888) M 8-8, 888.
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