Total synthesis of siomycin A: completion of the total synthesis.
The total synthesis of siomycin A (1), a representative compound of the thiostrepton family of peptide antibiotics, was achieved by incorporating the five synthetic segments A (2), B (3), C (4), D (5), and E (6). The dehydropiperidine segment A (2) was esterified with the dihydroquinoline segment C (4), and the subsequent coupling with the beta-phenylselenoalanine dipeptide segment D (5) at the segment C portion followed by lactamization between the segments A and D gave segment A-C-D (27). This was amidated with the pentapeptide segment B (3) at the segment A portion followed by one-pot cyclization (between segments A and B) and elongation (with the beta-phenylselenoalanine dipeptide segment E (6) at the segment A portion), thus furnishing siomycin A (1).
Mori
Tomonori
T
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
Higashibayashi
Shuhei
S
Goto
Taiji
T
Kohno
Mitsunori
M
Satouchi
Yukiko
Y
Shinko
Kazuyuki
K
Suzuki
Kengo
K
Suzuki
Shunya
S
Tohmiya
Hiraku
H
Hashimoto
Kimiko
K
Nakata
Masaya
M
D000588:Amines / Q000737:chemistry; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry; D006865:Hydrogenation; D007536:Isomerism; D008956:Models, Chemical; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D018036:Selenium Compounds / Q000737:chemistry
D000588:Amines; D004852:Epoxy Compounds; D010455:Peptides; D018036:Selenium Compounds; C024711:siomycin A