Issue 40, 2012
From the journal:

Organic & Biomolecular Chemistry

Organocatalytic asymmetric syntheses of inthomycins A, B and C†

Madoka Yoshino,a   Kohei Eto,a   Keisuke Takahashi,a   Jun Ishiharaa  and  Susumi Hatakeyama*a  

* Corresponding authors

a Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-Machi, Nagasaki 852-8521, Japan
E-mail: susumi@nagasaki-u.ac.jp
Fax: +81-95-819-2426
Tel: +81-95-819-2426

Abstract

The total syntheses of (+)-inthomycin A, (+)-inthomycin B and (−)-inthomycin C, the oxazole-triene antibiotics isolated from Streptomyces sp., have been accomplished via the highly enantio- and stereoselective construction of the C1–C7 (iododienyl)aldol units by taking advantage of a Cinchona alkaloid-catalyzed asymmetric β-lactone synthesis and their isomerisation-free Stille coupling with (E)-5-(3-(tributylstannyl)allyl)oxazole.

Graphical abstract: Organocatalytic asymmetric syntheses of inthomycins A, B and C

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Article information

DOI
https://doi.org/10.1039/C2OB26084K
Article type
Paper
Submitted
05 Jun 2012
Accepted
29 Aug 2012
First published
30 Aug 2012

Org. Biomol. Chem., 2012,10, 8164-8174

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Organocatalytic asymmetric syntheses of inthomycins A, B and C

M. Yoshino, K. Eto, K. Takahashi, J. Ishihara and S. Hatakeyama, Org. Biomol. Chem., 2012, 10, 8164 DOI: 10.1039/C2OB26084K

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