Total synthesis of the proposed structure for pyragonicin.
[structure: see text] The total synthesis of acetogenin 1 reported for pyragonicin and its 10-epimer 32 is described. The common THP ring system was stereoselectively constructed through a SmI(2)-induced reductive cyclization of beta-alkoxy acrylate 5 followed by Mitsunobu inversion, and each chiral center at C-10 was created by Brown's asymmetric allylation. Compound 1 had spectroscopic data consistent with that of natural pyragonicin, but a different optical rotation.
Takahashi
Shunya
S
RIKEN (The Institute of Physical and Chemical Research), Wako, Saitama 351-0198, Japan. shunyat@postman.riken.go.jp
Ogawa
Narihito
N
Koshino
Hiroyuki
H
Nakata
Tadashi
T
D054378:Acetogenins; D029061:Annonaceae / Q000737:chemistry; D003500:Cyclization; D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D054378:Acetogenins; D005233:Fatty Alcohols; D005663:Furans; D007783:Lactones; C509193:pyragonicin