Synthesis 2020; 52(10): 1541-1543
DOI: 10.1055/s-0037-1610752
paper
© Georg Thieme Verlag Stuttgart · New York

The Dianion of Dehydroacetic Acid: A Direct Synthesis of Pogopyrone A

Shuai Wang
,
Department of Chemistry, Iowa State University, Ames, IA 50010, USA   Email: gakraus@iastate.edu
› Author Affiliations
We thank KeyPlex for partial support of this work.
Further Information

Publication History

Received: 07 January 2020

Accepted after revision: 28 January 2020

Publication Date:
12 February 2020 (online)


Abstract

Dehydroacetic acid was converted into a silyl enol ether and titanium enolate. These reacted effectively with aldehydes and N-bromosuccinimide. Oxidation of the adduct with benzaldehyde afforded pogopyrone A in excellent overall yield.

Supporting Information

 
  • References

  • 1 Fadda AA, Elattar KM. Synth. Commun. 2016; 46: 1
  • 2 Chalaça MZ, Figueroa-Villar JD, Ellena JA, Castellano EE. Inorg. Chim. Acta 2002; 328: 45
  • 3 Harris TM, Harris CM. Chem. Commun. 1966; 699
  • 4 Ricardo L, Konstantinos AA, Doundoulakis T, Simonsen KB, Webber SE, Xiang AX. Heterocycles 2006; 68: 1099
  • 5 Lechani N, Hamdi M, Kheddis-Boutemeur B, Talhi O, Laichi Y, Bachari K, Silva AM. S. Synlett 2018; 29: 1502
  • 6 Thailambal VG, Pattabhi V, Gabe EJ. Acta Crystallogr., Sect. C 1986; 42: 1017