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Total synthesis of phomazarin

Publication ,  Journal Article
Boger, DL; Hong, J; Hikota, M; Ishida, M
Published in: Journal of the American Chemical Society
March 24, 1999

A concise total synthesis of phomazarin (1) is detailed enlisting a heterocyclic azadiene inverse electron demand Diels-Alder reaction (1,2,4- triazine → pyridine) for preparation of the fully substituted and appropriately functionalized pyridine C-ring. Thus, [4 + 2] cycloaddition (85%) of triethyl 1,2,4-triazine3,5,6-tricarboxylate (2) with trimethoxyethylene (3) followed by conversion of the cycloadduct 11 to the cyclic anhydride 13 provided the phomazarin C-ring with the three carboxylates suitably differentiated. Linkage of the A- and C-rings through selective nucleophilic addition of the aryllithium reagent 9 to the least hindered anhydride carbonyl of 13 followed by Friedel-Crafts closure of the B-ring provided the fully functionalized phomazarin skeleton. The successful structural correlation of synthetic 1 with natural material and its derivatives confirmed the latest structural assignment for the natural product.

Duke Scholars

Published In

Journal of the American Chemical Society

DOI

ISSN

0002-7863

Publication Date

March 24, 1999

Volume

121

Issue

11

Start / End Page

2471 / 2477

Related Subject Headings

  • General Chemistry
  • 40 Engineering
  • 34 Chemical sciences
  • 03 Chemical Sciences
 

Citation

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Boger, D. L., Hong, J., Hikota, M., & Ishida, M. (1999). Total synthesis of phomazarin. Journal of the American Chemical Society, 121(11), 2471–2477. https://doi.org/10.1021/ja983631q
Boger, D. L., J. Hong, M. Hikota, and M. Ishida. “Total synthesis of phomazarin.” Journal of the American Chemical Society 121, no. 11 (March 24, 1999): 2471–77. https://doi.org/10.1021/ja983631q.
Boger DL, Hong J, Hikota M, Ishida M. Total synthesis of phomazarin. Journal of the American Chemical Society. 1999 Mar 24;121(11):2471–7.
Boger, D. L., et al. “Total synthesis of phomazarin.” Journal of the American Chemical Society, vol. 121, no. 11, Mar. 1999, pp. 2471–77. Scopus, doi:10.1021/ja983631q.
Boger DL, Hong J, Hikota M, Ishida M. Total synthesis of phomazarin. Journal of the American Chemical Society. 1999 Mar 24;121(11):2471–2477.
Journal cover image

Published In

Journal of the American Chemical Society

DOI

ISSN

0002-7863

Publication Date

March 24, 1999

Volume

121

Issue

11

Start / End Page

2471 / 2477

Related Subject Headings

  • General Chemistry
  • 40 Engineering
  • 34 Chemical sciences
  • 03 Chemical Sciences