DOI: 10.1002/ange.201304624. Total Synthesis of Vinigrol

10.1002/ange.201304624

Crossref journal-article

Wiley

Angewandte Chemie (311)

Bibliography

Yang, Q., Njardarson, J. T., Draghici, C., & Li, F. (2013). Total Synthesis of Vinigrol. Angewandte Chemie, 125(33), 8810â8813. Portico.

Authors 4

Qingliang Yang (first)
Jon T. Njardarson (additional)
Cristian Draghici (additional)
Fang Li (additional)

References 67 Referenced 21

10.1021/jo00232a048
10.7164/antibiotics.41.25
10.7164/antibiotics.41.31
D. B.Norris P.Depledge A. P.Jackson PCT Int. Appl. WO 9107 953 1991.
H.Nakajima N.Yamamoto T.Kaizu T.Kino Jpn. Kokai Tokkyo Koho JP 07206668 1995;
J. T.Keane PCT Int. Appl. WO 20011000229 2001;
H.Onodera M.Ichimura K.Sakurada A.Kawabata T.Ota PCT Int. Appl. WO 2006077954 2006;
H.Onodera M.Ichimura K.Sakurada A.Kawabata T.Ota PCT Int. Appl. WO 2006077954.
10.1021/jo00061a002
10.1016/0040-4039(95)02032-2
{'key': 'e_1_2_2_14_2', 'first-page': '32', 'author': 'Devaux J.‐F.', 'year': '1996', 'journal-title': 'J. Chem. Res. Synth.'} / J. Chem. Res. Synth. by Devaux J.‐F. (1996)
10.1055/s-1996-5557
10.1055/s-1996-5697
10.1021/jo970343o
10.1055/s-1997-748
10.1016/S0040-4039(97)10750-X
10.1016/S0040-4020(99)00885-6
10.1021/ol034217k
10.1021/ol035283p
10.1021/jo0301301
10.1016/j.tetlet.2004.06.071
10.1021/jo048458x
10.1021/jo0484575
10.1021/jo048456c
10.1021/jo051318i
10.1021/ol0702977
10.1021/ol702202b
10.1002/ange.200800167
10.1002/anie.200800167
{'key': 'e_1_2_2_32_2', 'first-page': '313', 'volume': '37', 'author': 'Tessier G.', 'year': '2007', 'journal-title': 'Org. Prep. Proced. Int.'} / Org. Prep. Proced. Int. by Tessier G. (2007)
{'key': 'e_1_2_2_33_2', 'first-page': '205', 'volume': '22', 'author': 'Harmata M.', 'year': '2009', 'journal-title': 'Chemtracts'} / Chemtracts by Harmata M. (2009)
10.1002/ange.200906826
10.1002/anie.200906826
10.1002/chem.201000916
10.1021/ja908194b
10.1002/ange.201108779
10.1002/anie.201108779
{'key': 'e_1_2_2_39_2', 'first-page': '23', 'author': 'Morton J. G. M.', 'year': '2009', 'journal-title': 'Synlett'} / Synlett by Morton J. G. M. (2009)
10.1016/j.tetlet.2009.01.134
10.1021/ol901519k
10.1080/00397919408020778
The compound8can be accessed in two steps from commercially available 3‐(trimethylsilyl)propargyl alcohol:
10.1021/jo00051a042
10.1016/S0022-328X(00)91989-2
10.1021/jo00297a025
10.1080/00397919908086017
The outcome of this Grignard addition was very sensitive to solvents. For example when ether was replaced with THF or MgBr2was omitted the diastereoselectivity plummeted.
10.1002/adsc.200700438
10.1016/S0040-4039(00)85367-8
10.1021/jo01069a609
10.1016/S0040-4039(01)81404-0
10.1021/ja01019a052
10.1021/ja01168a044
{'key': 'e_1_2_2_56_2', 'first-page': '83', 'volume': '7', 'author': 'Bulman P. C.', 'year': '1991', 'journal-title': 'Comp. Org. Synth.'} / Comp. Org. Synth. by Bulman P. C. (1991)
10.1021/ol802421d
10.1039/c39910000818
10.1246/cl.1976.1263
10.1016/S0040-4039(01)94954-8
10.1002/ange.19921041013
10.1002/anie.199213451
Our spectral and physical data excellently matched that of a sample of vinigrol graciously shared with us by Professor Phil S. Baran (see the Supporting Information for more details).

Dates

Type	When
Created	12 years, 1 month ago (July 1, 2013, 11:28 a.m.)
Deposited	1 year, 10 months ago (Oct. 17, 2023, 11:53 a.m.)
Indexed	1 year, 10 months ago (Oct. 18, 2023, 12:37 a.m.)
Issued	12 years, 1 month ago (July 1, 2013)
Published	12 years, 1 month ago (July 1, 2013)
Published Online	12 years, 1 month ago (July 1, 2013)
Published Print	12 years ago (Aug. 12, 2013)

Funders 0

None

BibTeX

@article{Yang_2013, title={Total Synthesis of Vinigrol}, volume={125}, ISSN={1521-3757}, url={http://dx.doi.org/10.1002/ange.201304624}, DOI={10.1002/ange.201304624}, number={33}, journal={Angewandte Chemie}, publisher={Wiley}, author={Yang, Qingliang and Njardarson, Jon T. and Draghici, Cristian and Li, Fang}, year={2013}, month=jul, pages={8810–8813} }

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