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

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:
OSTI Identifier:
1257348
Grant/Contract Number:
AC02-05CH11231; S10-RR027172; 1341894
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
Research Org:
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
Sponsoring Org:
USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY