The first total synthesis of lactonamycin, a hexacyclic antitumor antibiotic

The total synthesis of lactonamycin has been achieved. The synthesis includes sequential intramolecular conjugate addition of alcohols to the acetylenic ester, stereoselective glycosylation of the tertiary alcohol, and Michael–Dieckmann type cyclization with the thioester, by which the highly conver...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2010-10, Vol.51 (42), p.5546-5549
Main Authors: Tatsuta, Kuniaki, Tanaka, Hiroaki, Tsukagoshi, Hitomi, Kashima, Takafumi, Hosokawa, Seijiro
Format: Article
Language:English
Subjects:
Alcohols
Antibiotics
Conjugates
Esters
Glycosylation
Lactonamycin
Michael–Dieckmann type annulation
Synthesis (chemistry)
Tetrahedrons
Thioester
Thioesters
Total synthesis
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 total synthesis of lactonamycin has been achieved. The synthesis includes sequential intramolecular conjugate addition of alcohols to the acetylenic ester, stereoselective glycosylation of the tertiary alcohol, and Michael–Dieckmann type cyclization with the thioester, by which the highly convergent route has been established.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.08.035