Total synthesis of a new cytotoxic acetogenin, jimenezin, and the revised structure.
The first total synthesis of jimenezin was achieved by using carbohydrates as chiral building blocks, thus revising the proposed structure 1 to 2. The key steps in this synthesis include an efficient construction of the THP-THF fragments 3 and 16 through a stereoselective condensation between the pyranyl aldehyde 5 and the acetylene derivative 6, and a palladium-catalyzed coupling reaction of 3 or 16 with a terminal butenolide 4.
Takahashi
S
S
RIKEN (The Institute of Physical and Chemical Research), Saitama, Japan. shunyat@riken.go.jp
Maeda
K
K
Hirota
S
S
Nakata
T
T
D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D019684:Magnoliopsida / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D012639:Seeds / Q000737:chemistry
D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; D007783:Lactones; D011714:Pyrans; C112079:isomurisolenin; C410435:jimenezin