TAXANE DITERPENES. 3: FORMATION OF THE EIGHT-MEMBERED B-RING BY SEMI-PINACOL REARRANGEMENT
Publication type: Journal Article
Publication date: 1996-11-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
The substituted furan carboxaldehyde 15 was converted into enone 20 via a stereoselective intramolecular pyrylium ylide-alkene cyclization. Subsequent elaboration of 20 into the triflate 23, followed by solvolysis in acidic trifluoroethanol resulted in quantitative rearrangement to the taxane B/C core 24. At a higher oxidation level 27 was ring expanded to give 28. The ring expansion strategy could also be initiated by β-elimination of the 3α, 10α-oxido bridge. Treatment of 50 with MeOH at reflux gave 52. Similar transformations in the 7-oxy series resulted in ring B expansion of 67 to give 68, and 75 to give 76.
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Total citations:
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Citations from 2024:
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(11.11%)
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Magnus P. et al. TAXANE DITERPENES. 3: FORMATION OF THE EIGHT-MEMBERED B-RING BY SEMI-PINACOL REARRANGEMENT // Tetrahedron. 1996. Vol. 52. No. 45. pp. 14147-14176.
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Magnus P., Diorazio L., Donohoe T. J., Giles M., Pye P., Tarrant J. G., Thom S. R. TAXANE DITERPENES. 3: FORMATION OF THE EIGHT-MEMBERED B-RING BY SEMI-PINACOL REARRANGEMENT // Tetrahedron. 1996. Vol. 52. No. 45. pp. 14147-14176.
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TY - JOUR
DO - 10.1016/0040-4020(96)00865-4
UR - https://doi.org/10.1016/0040-4020(96)00865-4
TI - TAXANE DITERPENES. 3: FORMATION OF THE EIGHT-MEMBERED B-RING BY SEMI-PINACOL REARRANGEMENT
T2 - Tetrahedron
AU - Magnus, Philip
AU - Diorazio, Louis
AU - Donohoe, Timothy J
AU - Giles, Melvyn
AU - Pye, Philip
AU - Tarrant, James G.
AU - Thom, Stephen R.
PY - 1996
DA - 1996/11/01
PB - Elsevier
SP - 14147-14176
IS - 45
VL - 52
SN - 0040-4020
SN - 1464-5416
ER -
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BibTex (up to 50 authors)
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@article{1996_Magnus,
author = {Philip Magnus and Louis Diorazio and Timothy J Donohoe and Melvyn Giles and Philip Pye and James G. Tarrant and Stephen R. Thom},
title = {TAXANE DITERPENES. 3: FORMATION OF THE EIGHT-MEMBERED B-RING BY SEMI-PINACOL REARRANGEMENT},
journal = {Tetrahedron},
year = {1996},
volume = {52},
publisher = {Elsevier},
month = {nov},
url = {https://doi.org/10.1016/0040-4020(96)00865-4},
number = {45},
pages = {14147--14176},
doi = {10.1016/0040-4020(96)00865-4}
}
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MLA
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Magnus, Philip, et al. “TAXANE DITERPENES. 3: FORMATION OF THE EIGHT-MEMBERED B-RING BY SEMI-PINACOL REARRANGEMENT.” Tetrahedron, vol. 52, no. 45, Nov. 1996, pp. 14147-14176. https://doi.org/10.1016/0040-4020(96)00865-4.