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The application of vinylogous iminium salt derivatives to a regiocontrolled and efficient relay synthesis of lukianol a and related marine natural products

✍ Scribed by John T. Gupton; Keith E. Krumpe; Bruce S. Burnham; Tammy M. Webb; Jordan S. Shuford; James A. Sikorski

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
566 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

Numerous novel pyrrole containing marine natural products have been shown to possess interesting biological properties These. compaunds have been the synthetic targets of several research groups and we have previously reported synthetic methods which utilize vinylogous iminium salt derivatives as building blocks for analogous pyrmle systems. We nuw report a novel and regiocontroltcd synthesis of a known pyrrole synthetic precursor to the compounds Lukianol A and Lammelarin 0 dimethyl ether hased on this synthetic methodology.

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The application of vinylogous iminium sa
The application of vinylogous iminium salts and related synthons to the regiocontrolled preparation of 2,3- and 2,5-disubstituted pyrroles
✍ John T Gupton; Scott A Petrich; Lana L Smith; Marc A Bruce; Phong Vu; Karen X Du πŸ“‚ Article πŸ“… 1996 πŸ› Elsevier Science 🌐 French βš– 640 KB

The reaction of 1-substituted vinamidinium sails with sarcosine ethyl ester produced 2,3-disubstituted pyrroles; a similar reaction with glycine ethyl ester gave 2,5-disubstituted pyrroles. Reactions of related thr~--carbon synthons with sarcosinΒ’ and glycine were studied under basic, neutral and ac