191993-23-4Relevant academic research and scientific papers
Total synthesis of (+)-4-deoxygigantecin
Makabe, Hidefumi,Tanaka, Akira,Oritani, Takayuki
, p. 6329 - 6340 (2007/10/03)
A total synthesis of a non-adjacent bis-tetrahydrofuranyl annonaceous acetogenin, (+)-4-deoxygigantecin (1) is described. Mono-tetrahydrofuran building block (10), of which the synthesis from (-)-muricatacin (8) had been described in an earlier report, was converted to bis-MOM ether (9) through two-step reactions. Transformation of this compound into non-adjacent bis- tetrahydrofuran unit (5) was carried out by a twelve-step sequence of reactions. Pd(0)-catalyzed cross coupling reaction between 5 and iodinated butenolide (7), which had been prepared from (S)-(-)-ethyl lactate, led to enyne (4). Finally, this compound was converted to (+)-4-deoxygigantecin (1) by two steps.
Total synthesis of (+)-4-deoxygigantecin
Makabe, Hidefumi,Tanaka, Akira,Oritani, Takayuki
, p. 4247 - 4250 (2007/10/03)
(+)-4-Deoxygigantecin (1) was totally synthesized from enantiomerically pure (-)-muricatacin (3). Thus, 3 afforded the key intermediate 5 through a five-step reaction sequence, which was then converted to (+)-4-deoxygigantecin (1) via the formation of bis-tetnhydrofuran unit 11 and a coupling reaction with iodo lactone synthon 16.
