Total synthesis of (+)-tubelactomicin A. 1. Stereoselective synthesis of the lower-half segment by an intramolecular Diels-Alder approach.
[reaction: see text]. Starting from diethyl (R)-malate, synthesis of the lower-half segment of (+)-tubelactomicin A, a 16-membered macrolide antibiotic, has been achieved. The synthesis involved the highly endo- and pi-facial selective intramolecular Diels-Alder reaction achieved using a trisubstituted methacrolein derivative tethering a 10-carbon dienyne unit at the beta-carbon, which in turn was prepared from a known allylated malic acid derivative.
Motozaki
Toru
T
Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
Sawamura
Kiyoto
K
Suzuki
Akari
A
Yoshida
Keigo
K
Ueki
Tatsuo
T
Ohara
Aiko
A
Munakata
Ryosuke
R
Takao
Ken-Ichi
K
Tadano
Kin-Ichi
K
D000190:Actinomyces / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008293:Malates / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D007783:Lactones; D018942:Macrolides; D008293:Malates; C418197:tubelactomicin A