Skip to main content

Structure and absolute configuration of plenolin: X-ray analysis of plenolin p-iodobenzoate

Publication ,  Journal Article
McPhail, AT; Onan, KD; Gross, PM
Published in: Journal of the Chemical Society, Perkin Transactions 2
January 1, 1975

The structure and absolute configuration of the cytotoxic pseudoguaianolide sesquiterpene lactone, plenolin (II), have been determined by X-ray analysis of the p-iodobenzoate derivative (III). Crystals of (III) are orthorhombic, space group P21212, with a = 9.29(1), b = 26.85(1), c = 8.45(1) Å, Z = 4. The structure was solved by the heavy-atom method and the atomic parameters refined by full-matrix least-squares calculations to R 0.041 over 1165 independent reflections from diffractometer measurements. The absolute configuration was established by the anomalous dispersion effect. The cycloheptane ring adopts a twist chair conformation, the γ-lactone ring is in an envelope conformation, and the cyclopentenone ring approximates a half-chair form.

Duke Scholars

Published In

Journal of the Chemical Society, Perkin Transactions 2

DOI

ISSN

1472-779X

Publication Date

January 1, 1975

Issue

5

Start / End Page

487 / 492

Related Subject Headings

  • Organic Chemistry
 

Citation

APA
Chicago
ICMJE
MLA
NLM
McPhail, A. T., Onan, K. D., & Gross, P. M. (1975). Structure and absolute configuration of plenolin: X-ray analysis of plenolin p-iodobenzoate. Journal of the Chemical Society, Perkin Transactions 2, (5), 487–492. https://doi.org/10.1039/P29750000487
McPhail, A. T., K. D. Onan, and P. M. Gross. “Structure and absolute configuration of plenolin: X-ray analysis of plenolin p-iodobenzoate.” Journal of the Chemical Society, Perkin Transactions 2, no. 5 (January 1, 1975): 487–92. https://doi.org/10.1039/P29750000487.
McPhail AT, Onan KD, Gross PM. Structure and absolute configuration of plenolin: X-ray analysis of plenolin p-iodobenzoate. Journal of the Chemical Society, Perkin Transactions 2. 1975 Jan 1;(5):487–92.
McPhail, A. T., et al. “Structure and absolute configuration of plenolin: X-ray analysis of plenolin p-iodobenzoate.” Journal of the Chemical Society, Perkin Transactions 2, no. 5, Jan. 1975, pp. 487–92. Scopus, doi:10.1039/P29750000487.
McPhail AT, Onan KD, Gross PM. Structure and absolute configuration of plenolin: X-ray analysis of plenolin p-iodobenzoate. Journal of the Chemical Society, Perkin Transactions 2. 1975 Jan 1;(5):487–492.

Published In

Journal of the Chemical Society, Perkin Transactions 2

DOI

ISSN

1472-779X

Publication Date

January 1, 1975

Issue

5

Start / End Page

487 / 492

Related Subject Headings

  • Organic Chemistry