Total synthesis of splenocin B, a potent inhibitor of the pro-inflammatory cytokine from marine-derived Streptomyces sp

The first total synthesis of splenocin B (1), a new potent anti-inflammatory antimycin-class antibiotic, has been described. The synthesis of 1 has been accomplished in 8 linear steps, starting from commercially available N-Boc-L-threonine benzyl ester 4 and 3,4-dihydroxypentanoic acid derivative 2....

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2015-12, Vol.71 (52), p.9626-9629
Main Authors: Yoshida, Ken-ichi, Ijiri, Minako, Iio, Hideo, Usuki, Yoshinosuke
Format: Article
Language:English
Subjects:
9-Membered dilactone
Anti-inflammatory
Antimycin-class antibiotics
Kita–Trost lactonization
Splenocin B
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The first total synthesis of splenocin B (1), a new potent anti-inflammatory antimycin-class antibiotic, has been described. The synthesis of 1 has been accomplished in 8 linear steps, starting from commercially available N-Boc-L-threonine benzyl ester 4 and 3,4-dihydroxypentanoic acid derivative 2. Kita–Trost lactonization via an ethoxyvinyl ester intermediate was utilized for the construction of the 9-membered dilactone core. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2015.10.075