Total syntheses of natural tubelactomicins B, D, and E: establishment of their stereochemistries.
Total syntheses of the antimicrobial tricyclic 16-membered macrolides, (+)-tubelactomicin B, (+)-tubelactomicin D, and (+)-tubelactomicin E, have been accomplished for the first time with common synthetic approaches. These total syntheses established the relative and absolute configurations of the three tubelactomicins, for which planar structures had solely been reported. The total synthesis of (+)-tubelactomicin D included a newly developed stereoselective intramolecular Diels-Alder reaction for constructing the highly functionalized octahydronaphthalene substructures.
Sawamura
Kiyoto
K
Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
Yoshida
Keigo
K
Suzuki
Akari
A
Motozaki
Toru
T
Kozawa
Ikuko
I
Hayamizu
Takashi
T
Munakata
Ryosuke
R
Takao
Ken-ichi
K
Tadano
Kin-ichi
K
D002625:Chemistry, Organic / Q000379:methods*; D003500:Cyclization; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008968:Molecular Conformation; D009281:Naphthalenes / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
D007783:Lactones; D018942:Macrolides; D009281:Naphthalenes; C523078:tubelactomicin B; C523081:tubelactomicin D; C523082:tubelactomicin E; C031721:naphthalene