Stereoselective divergent synthesis of four diastereomers of pachastrissamine (Jaspine B)

Yuji Yoshimitsu, Shinsuke Inuki, Shinya Oishi, Nobutaka Fujii, Hiroaki Ohno

Research output: Contribution to journalArticle

48 Citations (Scopus)

Abstract

Figure presented A divergent short synthesis of four diastereomers of pachastrissamine was achieved. Natural pachastrissamine was synthesized through bis-tosylation of the common intermediate and cyclization. 2-epi- Pachastrissamine was obtained by monotosylation and spontaneous cyclization of d-ribo-phytosphingosine derivative. By use of regio- and stereospecific ring-opening reaction of the orthoester assisted by a Boc group as a key step, 3-epi- and 2,3-epi-pachastrissamines were synthesized. The three stereogenic centers of all the diastereomers were constructed by using Garners aldehyde as the sole chiral source.

Original languageEnglish
Pages (from-to)3843-3846
Number of pages4
JournalJournal of Organic Chemistry
Volume75
Issue number11
DOIs
Publication statusPublished - 2010 Jun 4
Externally publishedYes

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phytosphingosine
Cyclization
Aldehydes
Derivatives
pachastrissamine

ASJC Scopus subject areas

  • Organic Chemistry

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Stereoselective divergent synthesis of four diastereomers of pachastrissamine (Jaspine B). / Yoshimitsu, Yuji; Inuki, Shinsuke; Oishi, Shinya; Fujii, Nobutaka; Ohno, Hiroaki.

In: Journal of Organic Chemistry, Vol. 75, No. 11, 04.06.2010, p. 3843-3846.

Research output: Contribution to journalArticle

Yoshimitsu, Yuji ; Inuki, Shinsuke ; Oishi, Shinya ; Fujii, Nobutaka ; Ohno, Hiroaki. / Stereoselective divergent synthesis of four diastereomers of pachastrissamine (Jaspine B). In: Journal of Organic Chemistry. 2010 ; Vol. 75, No. 11. pp. 3843-3846.
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AU - Ohno, Hiroaki

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