Stereocontrolled Total Synthesis of (+)-Isolaurenidificin and (−)-Bromlaurenidificin

Stereocontrolled Total Synthesis of (+)-Isolaurenidificin and (−)-Bromlaurenidificin

We report the first total syntheses of (+)-isolaurenidificin (1) and (−)-bromlaurenidificin (2), the latest acetogenins of the 2,6-dioxabicyclo[3.3.0]­octane class. The synthesis features a completely stereoselective one-pot epimerization-ring contraction to establish the cis configuration with resp...

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Veröffentlicht in:Journal of organic chemistry 2019-12, Vol.84 (23), p.15549-15556
Hauptverfasser: Kobayashi, Shoji, Hori, Yutaka, Yoneyama, Ryo, Tamura, Tomoki, Masuyama, Araki
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container_end_page 15556
container_issue 23
container_start_page 15549
container_title Journal of organic chemistry
container_volume 84
creator Kobayashi, Shoji
Hori, Yutaka
Yoneyama, Ryo
Tamura, Tomoki
Masuyama, Araki
description We report the first total syntheses of (+)-isolaurenidificin (1) and (−)-bromlaurenidificin (2), the latest acetogenins of the 2,6-dioxabicyclo[3.3.0]­octane class. The synthesis features a completely stereoselective one-pot epimerization-ring contraction to establish the cis configuration with respect to C10–H and C12–H of the tetrahydrofuran ring. Six stereogenic centers and an olefin geometry were constructed in a highly stereoselective manner. Absolute configurations of the natural products were deduced by the comparison of NMR data and specific rotations.
doi_str_mv 10.1021/acs.joc.9b02532
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title Stereocontrolled Total Synthesis of (+)-Isolaurenidificin and (−)-Bromlaurenidificin
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