Total synthesis of khafrefungin using highly stereoselective vinylogous Mukaiyama aldol reaction

Shin Ichi Shirokawa, Mariko Shinoyama, Isao Ooi, Seijiro Hosokawa, Atsuo Nakazaki, Susumu Kobayashi

Research output: Contribution to journalArticle

48 Citations (Scopus)

Abstract

(Chemical Equation Presented) A convergent total synthesis of khafrefungin was accomplished on the basis of (1) the highly stereoselective TiCl 4-mediated vinylogous Mukaiyama aldol reaction using vinylketene silyl N,O-acetal and (2) syn-selective aldol reaction of enal 5a and ethyl ketone 6 followed by anti-dehydration under Mitsunobu conditions.

Original languageEnglish
Pages (from-to)849-852
Number of pages4
JournalOrganic Letters
Volume9
Issue number5
DOIs
Publication statusPublished - 2007 Mar 1
Externally publishedYes

Fingerprint

acetals
Acetals
synthesis
Ketones
Dehydration
ketones
dehydration
3-hydroxybutanal
khafrefungin

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Total synthesis of khafrefungin using highly stereoselective vinylogous Mukaiyama aldol reaction. / Shirokawa, Shin Ichi; Shinoyama, Mariko; Ooi, Isao; Hosokawa, Seijiro; Nakazaki, Atsuo; Kobayashi, Susumu.

In: Organic Letters, Vol. 9, No. 5, 01.03.2007, p. 849-852.

Research output: Contribution to journalArticle

Shirokawa, Shin Ichi ; Shinoyama, Mariko ; Ooi, Isao ; Hosokawa, Seijiro ; Nakazaki, Atsuo ; Kobayashi, Susumu. / Total synthesis of khafrefungin using highly stereoselective vinylogous Mukaiyama aldol reaction. In: Organic Letters. 2007 ; Vol. 9, No. 5. pp. 849-852.
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