Tetrahedron p. 6329 - 6340 (1998)
Update date:2022-08-03
Topics:
Makabe, Hidefumi
Tanaka, Akira
Oritani, Takayuki
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.
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Doi:10.1021/ic9800280
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