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Title: Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a Scalemic Mixture

Abstract

We prepared the enantiomers of the natural product cycloprodigiosin using an expedient five-step synthetic sequence that takes advantage of a Schöllkopf–Barton–Zard (SBZ) pyrrole annulation with a chiral isocyanoacetate and a nitrocyclohexene derivative. Using chiral HPLC and X-ray crystallographic analyses of the synthetically prepared material and natural isolate (isolated from the marine bacterium Pseudoalteromonas rubra), naturally occurring cycloprodigiosin was determined to be a scalemic mixture occurring in an enantiomeric ratio of 83:17 (R)/(S) at C4'.

Authors:
; ; ; ;
Publication Date:
Research Org.:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)
OSTI Identifier:
1257348
Grant/Contract Number:  
AC02-05CH11231; S10-RR027172; 1341894
Resource Type:
Accepted Manuscript
Journal Name:
Organic Letters
Additional Journal Information:
Journal Volume: 17; Journal Issue: 14; Journal ID: ISSN 1523-7060
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Johnson, Rebecca E., de Rond, Tristan, Lindsay, Vincent N. G., Keasling, Jay D., and Sarpong, Richmond. Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a Scalemic Mixture. United States: N. p., 2015. Web. doi:10.1021/acs.orglett.5b01527.
Johnson, Rebecca E., de Rond, Tristan, Lindsay, Vincent N. G., Keasling, Jay D., & Sarpong, Richmond. Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a Scalemic Mixture. United States. doi:10.1021/acs.orglett.5b01527.
Johnson, Rebecca E., de Rond, Tristan, Lindsay, Vincent N. G., Keasling, Jay D., and Sarpong, Richmond. Fri . "Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a Scalemic Mixture". United States. doi:10.1021/acs.orglett.5b01527. https://www.osti.gov/servlets/purl/1257348.
@article{osti_1257348,
title = {Synthesis of Cycloprodigiosin Identifies the Natural Isolate as a Scalemic Mixture},
author = {Johnson, Rebecca E. and de Rond, Tristan and Lindsay, Vincent N. G. and Keasling, Jay D. and Sarpong, Richmond},
abstractNote = {We prepared the enantiomers of the natural product cycloprodigiosin using an expedient five-step synthetic sequence that takes advantage of a Schöllkopf–Barton–Zard (SBZ) pyrrole annulation with a chiral isocyanoacetate and a nitrocyclohexene derivative. Using chiral HPLC and X-ray crystallographic analyses of the synthetically prepared material and natural isolate (isolated from the marine bacterium Pseudoalteromonas rubra), naturally occurring cycloprodigiosin was determined to be a scalemic mixture occurring in an enantiomeric ratio of 83:17 (R)/(S) at C4'.},
doi = {10.1021/acs.orglett.5b01527},
journal = {Organic Letters},
number = 14,
volume = 17,
place = {United States},
year = {2015},
month = {7}
}

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