Total Syntheses of (−)-Herbertenediol, (−)-Mastigophorene A, and (−)-Mastigophorene B. Combined Utility of Chiral Bicyclic Lactams and Chiral Aryl Oxazolines
Publication type: Journal Article
Publication date: 1999-03-01
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
A nonracemic bicyclic lactam has been used to construct a chiral cyclopentane containing vicinal quaternary carbon centers in optically pure form, which is common to all of the title compounds. An oxazoline-mediated asymmetric Ullmann coupling was then utilized to establish chirality about the biaryl axis of mastigophorenes A and B. Through the course of this synthesis, it was clearly demonstrated that smaller chiral auxiliaries lead to higher levels of atroposelection, a previously unknown phenomenon of the asymmetric Ullmann coupling.
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Metrics
87
Total citations:
87
Citations from 2024:
6
(6.9%)
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MLA
Cite this
GOST
Copy
Degnan A. P., Meyers A. Total Syntheses of (−)-Herbertenediol, (−)-Mastigophorene A, and (−)-Mastigophorene B. Combined Utility of Chiral Bicyclic Lactams and Chiral Aryl Oxazolines // Journal of the American Chemical Society. 1999. Vol. 121. No. 12. pp. 2762-2769.
GOST all authors (up to 50)
Copy
Degnan A. P., Meyers A. Total Syntheses of (−)-Herbertenediol, (−)-Mastigophorene A, and (−)-Mastigophorene B. Combined Utility of Chiral Bicyclic Lactams and Chiral Aryl Oxazolines // Journal of the American Chemical Society. 1999. Vol. 121. No. 12. pp. 2762-2769.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/ja984182x
UR - https://doi.org/10.1021/ja984182x
TI - Total Syntheses of (−)-Herbertenediol, (−)-Mastigophorene A, and (−)-Mastigophorene B. Combined Utility of Chiral Bicyclic Lactams and Chiral Aryl Oxazolines
T2 - Journal of the American Chemical Society
AU - Degnan, Andrew P
AU - Meyers, A.I
PY - 1999
DA - 1999/03/01
PB - American Chemical Society (ACS)
SP - 2762-2769
IS - 12
VL - 121
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{1999_Degnan,
author = {Andrew P Degnan and A.I Meyers},
title = {Total Syntheses of (−)-Herbertenediol, (−)-Mastigophorene A, and (−)-Mastigophorene B. Combined Utility of Chiral Bicyclic Lactams and Chiral Aryl Oxazolines},
journal = {Journal of the American Chemical Society},
year = {1999},
volume = {121},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/ja984182x},
number = {12},
pages = {2762--2769},
doi = {10.1021/ja984182x}
}
Cite this
MLA
Copy
Degnan, Andrew P., and A.I Meyers. “Total Syntheses of (−)-Herbertenediol, (−)-Mastigophorene A, and (−)-Mastigophorene B. Combined Utility of Chiral Bicyclic Lactams and Chiral Aryl Oxazolines.” Journal of the American Chemical Society, vol. 121, no. 12, Mar. 1999, pp. 2762-2769. https://doi.org/10.1021/ja984182x.