Total synthesis of paniculide a from D-glucose

Seiji Amano, Noriaki Takemura, Masami Ohtsuka, Seiichiro Ogawa, Noritaka Chida

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

The chiral total synthesis of paniculide A (1), a highly oxygenated sesquiterpene possessing a bisabolane skeleton, starting from D-glucose is described. The two different approaches, both involved Ferrier's carbocyclization reaction to construct the cyclohexane unit in 1, were explored. The first approach, employing the carbocyclization of bicyclic substrate furnished the formal total synthesis. The second approach, designed to suppress the undesired side reactions observed in the first one, adopted the carbocyclization of a monocyclic substrate, and Claisen rearrangement for the stereoselective carbon-carbon bond formation. The successful total synthesis of I revealed the effectiveness of the combination of Ferrier's carbocyclization and Claisen rearrangement for the chiral synthesis of highly oxygenated natural products possessing cyclohexane units.

Original languageEnglish
Pages (from-to)3855-3870
Number of pages16
JournalTetrahedron
Volume55
Issue number13
DOIs
Publication statusPublished - 1999 Mar 26

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Carbon
Glucose
Sesquiterpenes
Biological Products
Skeleton
Substrates
Cyclohexane

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Amano, S., Takemura, N., Ohtsuka, M., Ogawa, S., & Chida, N. (1999). Total synthesis of paniculide a from D-glucose. Tetrahedron, 55(13), 3855-3870. https://doi.org/10.1016/S0040-4020(99)00096-4

Total synthesis of paniculide a from D-glucose. / Amano, Seiji; Takemura, Noriaki; Ohtsuka, Masami; Ogawa, Seiichiro; Chida, Noritaka.

In: Tetrahedron, Vol. 55, No. 13, 26.03.1999, p. 3855-3870.

Research output: Contribution to journalArticle

Amano, S, Takemura, N, Ohtsuka, M, Ogawa, S & Chida, N 1999, 'Total synthesis of paniculide a from D-glucose', Tetrahedron, vol. 55, no. 13, pp. 3855-3870. https://doi.org/10.1016/S0040-4020(99)00096-4
Amano S, Takemura N, Ohtsuka M, Ogawa S, Chida N. Total synthesis of paniculide a from D-glucose. Tetrahedron. 1999 Mar 26;55(13):3855-3870. https://doi.org/10.1016/S0040-4020(99)00096-4
Amano, Seiji ; Takemura, Noriaki ; Ohtsuka, Masami ; Ogawa, Seiichiro ; Chida, Noritaka. / Total synthesis of paniculide a from D-glucose. In: Tetrahedron. 1999 ; Vol. 55, No. 13. pp. 3855-3870.
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