학술논문

Highly Diastereoselective Desymmetrizations of Cyclo(Pro,Pro): An Enantioselective Strategy toward Phakellstatin and Phakellin

Document Type

Article

Author

Poullennec, K. G.; Kelly, A. T.; Romo, D.

Source

Organic Letters; August 2002, Vol. 4 Issue: 16 p2645-2648, 4p

Subject

Language

ISSN

15237060; 15237052

Abstract

Monoenolates of C2-symmetric, proline-derived piperazine-2,5-diones were generated and trapped with a variety of electrophiles to produce, in a highly diastereoselective fashion, functionalized diketopiperazines (DKPs). These reactions provide the basis for an asymmetric, desymmetrization strategy toward the marine alkaloids phakellstatin and phakellin. The relative stereochemistry of the functionalized DKPs was confirmed by single-crystal X-ray analysis and/or NOE experiments. Bis-functionalization of the DKPs was also found to proceed with high levels of diastereoselectivity.

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