Enantioselective total synthesis of convolutamydines B and E

Tomoaki Nakamura, Shin Ichi Shirokawa, Seijiro Hosokawa, Atsuo Nakazaki, Susumu Kobayashi

Research output: Contribution to journalArticle

97 Citations (Scopus)

Abstract

The first enantioselective total synthesis of convolutamydines B and E has been achieved using our vinylogous Mukaiyama aldol reaction. The synthesis features highly diastereoselective vinylogous Mukaiyama aldol reaction with isatin instead of aldehydes to construct a chiral center of convolutamydines. Additionally, the absolute configuration of natural convolutamydine B has been determined as R by its CD spectrum.

Original languageEnglish
Pages (from-to)677-679
Number of pages3
JournalOrganic Letters
Volume8
Issue number4
DOIs
Publication statusPublished - 2006 Feb 16
Externally publishedYes

Fingerprint

Isatin
synthesis
aldehydes
Aldehydes
configurations
convolutamydine B
3-hydroxybutanal
convolutamydine E

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Nakamura, T., Shirokawa, S. I., Hosokawa, S., Nakazaki, A., & Kobayashi, S. (2006). Enantioselective total synthesis of convolutamydines B and E. Organic Letters, 8(4), 677-679. https://doi.org/10.1021/ol052871p

Enantioselective total synthesis of convolutamydines B and E. / Nakamura, Tomoaki; Shirokawa, Shin Ichi; Hosokawa, Seijiro; Nakazaki, Atsuo; Kobayashi, Susumu.

In: Organic Letters, Vol. 8, No. 4, 16.02.2006, p. 677-679.

Research output: Contribution to journalArticle

Nakamura, T, Shirokawa, SI, Hosokawa, S, Nakazaki, A & Kobayashi, S 2006, 'Enantioselective total synthesis of convolutamydines B and E', Organic Letters, vol. 8, no. 4, pp. 677-679. https://doi.org/10.1021/ol052871p
Nakamura T, Shirokawa SI, Hosokawa S, Nakazaki A, Kobayashi S. Enantioselective total synthesis of convolutamydines B and E. Organic Letters. 2006 Feb 16;8(4):677-679. https://doi.org/10.1021/ol052871p
Nakamura, Tomoaki ; Shirokawa, Shin Ichi ; Hosokawa, Seijiro ; Nakazaki, Atsuo ; Kobayashi, Susumu. / Enantioselective total synthesis of convolutamydines B and E. In: Organic Letters. 2006 ; Vol. 8, No. 4. pp. 677-679.
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