Total synthesis of Deoxy-solomonamide B by mimicking biogenesis.
A total synthesis of Deoxy-solomonamide B was accomplished starting from tryptophan in an efficient manner by mimicking the proposed biogenetic route. The present synthesis utilizes a crotylation, oxidative cleavage of the indole moiety, and macrolactamization as key steps. The use of the indole nucleus as a masked anthranilic acid unit paves the way for the easy synthesis of related macrocycles and natural products where the ortho-acyl aniline moiety is embedded into them, which otherwise is difficult to synthesize.
CSIR-National Chemical Laboratory, Division of Organic Chemistry, Dr. Homi Bhabha Road, Pune, 411008, India.
N
N
Vasudevan
CSIR-National Chemical Laboratory, Division of Organic Chemistry, Dr. Homi Bhabha Road, Pune, 411008, India.
K
K
Kashinath
CSIR-National Chemical Laboratory, Division of Organic Chemistry, Dr. Homi Bhabha Road, Pune, 411008, India.
D Srinivasa
DS
Reddy
D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D047232:Theonella / Q000737:chemistry; D014364:Tryptophan / Q000031:analogs & derivatives / Q000737:chemistry
D001688:Biological Products; D007211:Indoles; D010456:Peptides, Cyclic; C558621:solomonamide B; C030374:indole; D014364:Tryptophan