An efficient method for the synthesis of versatile intermediates leading to 13-deoxy- and 9,13-dideoxyphorbols

Akihiro Sekine, Naoya Kumagai, Koichiro Uotsu, Takashi Ohshima, Masakatsu Shibasaki

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

An efficient method for the synthesis of versatile intermediates for biologically interesting 13-deoxy- and 9,13-dideoxyphorbol ester analogs is described. First, more efficient synthetic routes to the bicyclic ketones 7 and 8, which are well-known intermediates for the synthesis of 13- deoxyphorbols, than the previous one were established. Second, 7 and 8 were successfully converted to the intermediates 19, 25 and 27 for the synthesis of 9,13-dideoxyphorbols using Peterson reaction, oxymercuration and nitrile oxide cycloaddition as key steps.

Original languageEnglish
Pages (from-to)509-513
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number4
DOIs
Publication statusPublished - Jan 22 2000
Externally publishedYes

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Nitriles
Cycloaddition Reaction
Ketones
Oxides
Esters
Cycloaddition

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

An efficient method for the synthesis of versatile intermediates leading to 13-deoxy- and 9,13-dideoxyphorbols. / Sekine, Akihiro; Kumagai, Naoya; Uotsu, Koichiro; Ohshima, Takashi; Shibasaki, Masakatsu.

In: Tetrahedron Letters, Vol. 41, No. 4, 22.01.2000, p. 509-513.

Research output: Contribution to journalArticle

Sekine, Akihiro ; Kumagai, Naoya ; Uotsu, Koichiro ; Ohshima, Takashi ; Shibasaki, Masakatsu. / An efficient method for the synthesis of versatile intermediates leading to 13-deoxy- and 9,13-dideoxyphorbols. In: Tetrahedron Letters. 2000 ; Vol. 41, No. 4. pp. 509-513.
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