Total synthesis of (+)-tubelactomicin A. 2. Synthesis of the upper-half segment and completion of the total synthesis.
[reaction: see text]. We have completed the total synthesis of natural (+)-tubelactomicin A (1), a 16-membered macrolide antibiotic. This Letter presents a highly efficient synthesis of the upper-half segment (C14-C24) and the completion of the total synthesis featuring a high-yielding Stille coupling for the connection of the upper-half and lower-half segments and Mukaiyama macrolactonization for the construction of the entire structure of 1.
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
D039903:Actinobacteria / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D007773:Lactates / 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; D007773:Lactates; D007783:Lactones; D018942:Macrolides; D008293:Malates; C418197:tubelactomicin A