Cytochalasins from an Australian Marine Sediment-Derived Phomopsis sp. (CMB-M0042F): Acid-Mediated Intramolecular Cycloadditions Enhance Chemical Diversity

Shang, Zhuo, Raju, Ritesh, Salim, Angela A., Khalil, Zeinab G. and Capon, Robert J. (2017) Cytochalasins from an Australian Marine Sediment-Derived Phomopsis sp. (CMB-M0042F): Acid-Mediated Intramolecular Cycloadditions Enhance Chemical Diversity. Journal of Organic Chemistry, 82 18: 9704-9709. doi:10.1021/acs.joc.7b01793


Author Shang, Zhuo
Raju, Ritesh
Salim, Angela A.
Khalil, Zeinab G.
Capon, Robert J.
Title Cytochalasins from an Australian Marine Sediment-Derived Phomopsis sp. (CMB-M0042F): Acid-Mediated Intramolecular Cycloadditions Enhance Chemical Diversity
Journal name Journal of Organic Chemistry   Check publisher's open access policy
ISSN 1520-6904
0022-3263
Publication date 2017-09-15
Year available 2017
Sub-type Article (original research)
DOI 10.1021/acs.joc.7b01793
Open Access Status Not yet assessed
Volume 82
Issue 18
Start page 9704
End page 9709
Total pages 6
Place of publication WASHINGTON
Publisher American Chemical Society
Language eng
Subject 1605 Organic Chemistry
Abstract Chemical analysis of an Australian coastal marine sediment-derived fungus, Phomopsis sp. (CMB-M0042F), yielded the known cytochalasins J (1) and H (2), together with five new analogues, cytochalasins J-J (3-5) and H and H (6 and 7). Structures of 1-7 were assigned on the basis of detailed spectroscopic analysis, chemical interconversion, and biosynthetic and mechanistic considerations. Of note, 1 and 2 proved to be highly sensitive to acid-mediated transformation, with 1 affording 3-5 and 2 affording 6 and 7. Whereas 1, 2, 4, and 5 were detected as natural products in crude culture extracts, 3, 6, and 7 were designated as acid-mediated handling artifacts. We propose novel stereo- and regiospecific intramolecular cycloadditions, under tight functional group control, that facilitate selective conversion of 1 and 2 to the rare 5/6/6/7/5- and 5/6/5/8-fused heterocycles 5 and 7, respectively. Knowledge of acid sensitivity within the cytochalasin family provides a valuable cautionary lesson that has the potential to inform our analysis of past and future investigations into this structure class and inspire novel biomimetic transformations leading to new chemical diversity.
Q-Index Code C1
Q-Index Status Provisional Code
Grant ID DP120100183
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collection: Scopus Import
 
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Created: Fri, 03 Nov 2017, 16:03:40 EST